5-Pentyl-1,3-benzenediol (Olivetol) [C11H16O2] by Asch

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Reactions (70)

Substances (78)

Targets (25)

Citations (44)

Conditions

References

Synthesize Find similar 92%

With boron tribromide in dichloromethane

T=-15 - 20°C; 1.5 h; Inert atmosphere; Hide Experimental Procedure

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Rx-ID: 271814 Find similar reactions

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas

Tetrahedron, 2017 , vol. 73, # 35 p. 5297 - 5301 Title/Abstract Full Text View citing articles Show Details

1,3-Dihydroxy-5-alkylbenzenes (3, 4, 5): general method

General procedure: To the solution of 1,3-dimethoxy-5-alkylbenzenes 8, 11, and 12,respectively, in dry dichloromethane was added dropwise 2.2 eq. of BBr3 (1 M solution in dichloromethane) at 15 °C and the reaction was stirred under argon atmosphere with temperature rising to r.t. over 1.5 h. The mixture was quenched with water, neutralized with NaHCO3 and extracted with dichloromethane. The organic phase was washed with water and brine and dried over MgSO4. After concentration in vacuo, the crude product was purified by silica gel column chromatography with petrol ether:ethyl acetate (9:1) as an eluent. The yields were 92percent for olivetol (3), 82percent for grevillol (4), and 86percent for cardol (adipostatin A, 6), respectively. 81%

With hydrogen bromide; acetic acid

3 h; Heating;

Alonso, Emma; Ramon, Diego J.; Yus, Miguel

Journal of Organic Chemistry, 1997 , vol. 62, # 2 p. 417 - 421 Title/Abstract Full Text View citing articles Show Details

61%

With lithium; ethylenediamine in tetrahydrofuran

T=8°C; 14 h;

Shindo, Takeyuki; Fukuyama, Yasuaki; Sugai, Takeshi

Synthesis, 2004 , # 5 p. 692 - 700 Title/Abstract Full Text View citing articles Show Details

With hydrogen iodide

Asahina

Chemische Berichte, 1936 , vol. 69, p. 1643,1644 Full Text View citing articles Show Details

Asahina; Nogami

Chemische Berichte, 1935 , vol. 68, p. 1500,1501, 2392 Yakugaku Zasshi, 1935 , vol. 55, p. 933,944 Full Text View citing articles Show Details

With phosphorus; hydrogen iodide

Asahina

Chemische Berichte, 1936 , vol. 69, p. 1643,1644 Full Text View citing articles Show Details

Asahina; Nogami

Chemische Berichte, 1935 , vol. 68, p. 1500,1501, 2392 Yakugaku Zasshi, 1935 , vol. 55, p. 933,944 Full Text View citing articles Show Details

With pyridine; hydrogenchloride

Petrzilka,T. et al.

Helvetica Chimica Acta, 1969 , vol. 52, # 4 p. 1102 - 1134 Full Text View citing articles Show Details

With pyridine hydrochloride; boron tribromide in dichloromethane

T=-78°C; 24 h;

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

With chloro-trimethyl-silane; sodium iodide in acetonitrile

36 h; Heating;

Ayer, William A.; Browne, Lois M.; Lovell, Sarah H.

Phytochemistry (Elsevier), 1983 , vol. 22, # 10 p. 2267 - 2272 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 338558 Find similar reactions

T=210 - 230°C;

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Adams; Hunt; Clark

Journal of the American Chemical Society, 1940 , vol. 62, p. 735,737 Full Text View citing articles Show Details

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Rx-ID: 384477 Find similar reactions

With sodium hydroxide

Anker; Cook

Journal of the Chemical Society, 1945 , p. 311 Full Text View citing articles Show Details

With sodium hydroxide

Korte,F.; Sieper,H.

Justus Liebigs Annalen der Chemie, 1960 , vol. 630, p. 71 - 83 Full Text View citing articles Show Details

With sodium hydroxide in water

Heating;

Kato,T.; Hozumi,T.

Chemical and Pharmaceutical Bulletin, 1972 , vol. 20, p. 1574 - 1578 Full Text View citing articles Show Details

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Rx-ID: 1061698 Find similar reactions

With N,N-dimethyl-formamide

Chandrasekharan,V. et al.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1978 , vol. 16, p. 970 - 972 Full Text View citing articles Show Details

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(i) CuBr2, DME, (ii) (heating in DMF), (iii) aq. NaOH; Multistep reaction;

Rx-ID: 1342766 Find similar reactions

Marmor,R.S.

Journal of Organic Chemistry, 1972 , vol. 37, # 18 p. 2901 - 2904 Full Text View citing articles Show Details

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Rx-ID: 1673493 Find similar reactions

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Kotnis, Atul S.

Tetrahedron Letters, 1991 , vol. 32, # 29 p. 3441 - 3444 Title/Abstract Full Text View citing articles Show Details

Yield given. Multistep reaction;

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Rx-ID: 2554705 Find similar reactions

With sodium hydroxide in methanol; water

Chan, T. H.; Chaly, T.

Tetrahedron Letters, 1982 , vol. 23, # 29 p. 2935 - 2938 Title/Abstract Full Text View citing articles Show Details

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With calcium carbonate in benzene

5 h; Heating;

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Rx-ID: 2964238 Find similar reactions

Jaxa-Chamiec, Albert A.; Sammes, Peter G.; Kennewell, Peter D.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 170 - 175 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 3487235 Find similar reactions

With sodium; butan-1-ol

T=80 - 90°C; 1 h;

Wu, Li-Qiang; Yang, Chun-Guang; Yang, Li-Ming; Yang, Li-Juan

Journal of Chemical Research, 2009 , # 3 p. 183 - 185 Title/Abstract Full Text View citing articles Show Details

With hydrogen; palladium on activated charcoal in ethanol

Yield given;

Anand; Ranjan

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1889 - 1890 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 6189901 Find similar reactions

Hide Experimental Procedure

Synthetic Technology Corporation

Patent: US5292899 A1, 1994 ; Title/Abstract Full Text Show Details

16:(FIG. 4A)

Synthesis of Tri-deuterated Olivetol 26 Intermediate; Step e Scheme III (FIG. 4A) To a solution of bismethylolivetol 31 (4.0 g, 19.0 mmol) was added dropwise a solution of boron tribromide (32 mL, 1M, 32 mmol) in methylene chloride at -78° C. After addition, the reaction mixture was stirred at -78° C. for 1 hour, then at 0° C. for 2 hours, and then at 23° C. overnight. The reaction was quenched with water at 0° C. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated on a rotavaporator. Chromatography of the dried material on a silica gel column with hexane-ether (3:1) offered olivetol-d3 26 (3.34 g), in 96percent yield. Focella; Teitel; Brossi

Journal of Organic Chemistry, 1977 , vol. 42, # 21 p. 3456 - 3457 Title/Abstract Full Text View citing articles Show Details

Hoffmann-La Roche

Patent: DE2002815 , 1970 ; Chem.Abstr., vol. 73, # 66258 Full Text Show Details

Baeckstroem; Sundstroem

Acta Chemica Scandinavica (1947-1973), 1970 , vol. 24, p. 716 Full Text Show Details

HOFFMANN-LA ROCHE INC.; Nutley; N. Y.

Patent: US3919322 , 1975 ; Chem.Abstr., 1975 , vol. 84, # 43460 Full Text Show Details

CIBA-GEIGY

Patent: FR2212317DE2359410 , 1974 ; Chem.Abstr., 1974 , vol. 81, # 91205

Full Text Show Details

Barker; Settine

Organic Preparations and Procedures International, 1979 , vol. 11, p. 87,90 Full Text Show Details

Krishnamurty; Prasad

Tetrahedron Letters, 1975 , p. 2511 Full Text View citing articles Show Details

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Rx-ID: 6189902 Find similar reactions

With sodium

T=140 - 150°C; Erhitzen des Reaktionsprodukts mit KOH auf 250grad;

Asahina; Asano

Chemische Berichte, 1932 , vol. 65, p. 475,581 Yakugaku Zasshi, 1932 , vol. 52, p. 417,428 Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 7924432 Find similar reactions

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Asahina; Asano

Chemische Berichte, 1932 , vol. 65, p. 475,581 Yakugaku Zasshi, 1932 , vol. 52, p. 417,428 Full Text View citing articles Show Details

Zopf

Justus Liebigs Annalen der Chemie, 1900 , vol. 313, p. 342 Beihefte zum botanischen Zentralblatt, 1903 , vol. 14, p. 1. Heft. S. 112 Full Text View citing articles Show Details

T=150°C; im Rohr;

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Rx-ID: 7924433 Find similar reactions

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Asahina; Asano

Chemische Berichte, 1932 , vol. 65, p. 475,581 Yakugaku Zasshi, 1932 , vol. 52, p. 417,428 Full Text View citing articles Show Details

Zopf

Justus Liebigs Annalen der Chemie, 1900 , vol. 313, p. 342 Beihefte zum botanischen Zentralblatt, 1903 , vol. 14, p. 1. Heft. S. 112 Full Text View citing articles Show Details

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Rx-ID: 17115413 Find similar reactions

Multi-step reaction with 5 steps 1: Et3N / tetrahydrofuran / 1 h / 0 - 20 °C 2: 41 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 3: 96 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 4: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 5: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

Alonso, Emma; Ramon, Diego J.; Yus, Miguel

Journal of Organic Chemistry, 1997 , vol. 62, # 2 p. 417 - 421 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: PBr3

2: CuI 3: aq. HCl, Py View Scheme

Petrzilka,T. et al.

Helvetica Chimica Acta, 1969 , vol. 52, # 4 p. 1102 - 1134 Full Text View citing articles Show Details

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Rx-ID: 17133050 Find similar reactions

Multi-step reaction with 4 steps 1: 41 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 2: 96 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 3: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 4: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

Alonso, Emma; Ramon, Diego J.; Yus, Miguel

Journal of Organic Chemistry, 1997 , vol. 62, # 2 p. 417 - 421 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 17133125 Find similar reactions

Multi-step reaction with 3 steps 1: 96 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 2: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 3: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

Alonso, Emma; Ramon, Diego J.; Yus, Miguel

Journal of Organic Chemistry, 1997 , vol. 62, # 2 p. 417 - 421 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 2: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

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Rx-ID: 17137054 Find similar reactions

Alonso, Emma; Ramon, Diego J.; Yus, Miguel

Journal of Organic Chemistry, 1997 , vol. 62, # 2 p. 417 - 421 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 18309104 Find similar reactions

Multi-step reaction with 3 steps 1: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 2: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 3: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

Ayer, William A.; Browne, Lois M.; Lovell, Sarah H.

Phytochemistry (Elsevier), 1983 , vol. 22, # 10 p. 2267 - 2272 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 18310647 Find similar reactions

Multi-step reaction with 2 steps 1: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 2: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

Ayer, William A.; Browne, Lois M.; Lovell, Sarah H.

Phytochemistry (Elsevier), 1983 , vol. 22, # 10 p. 2267 - 2272 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 18318648 Find similar reactions

Multi-step reaction with 5 steps 1: 89 percent / (COCl)2 / benzene / 2 h, room t., 1 h, reflux 2: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 3: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 4: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 5: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

Ayer, William A.; Browne, Lois M.; Lovell, Sarah H.

Phytochemistry (Elsevier), 1983 , vol. 22, # 10 p. 2267 - 2272 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 7 steps 4: 28.8 g / fluoroboric acid, sodium nitrite / H2O 5: 7.6 g / warming, distillation 6: 60 percent / lithium chips / 0.5 h 7: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 4 steps 1: LiAlH4

2: PBr3

Petrzilka,T. et al.

Helvetica Chimica Acta, 1969 , vol. 52, # 4 p. 1102 - 1134 Full Text View citing articles Show Details

3: CuI 4: aq. HCl, Py View Scheme

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Rx-ID: 18318668 Find similar reactions

Multi-step reaction with 4 steps 1: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 2: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 3: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 4: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

Ayer, William A.; Browne, Lois M.; Lovell, Sarah H.

Phytochemistry (Elsevier), 1983 , vol. 22, # 10 p. 2267 - 2272 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 6 steps 3: 28.8 g / fluoroboric acid, sodium nitrite / H2O 4: 7.6 g / warming, distillation 5: 60 percent / lithium chips / 0.5 h 6: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 92 percent / diethyl ether / 2 h / Ambient temperature 2: p-toluenesulfonic acid / benzene / Heating 3: H2 / 10percent Pd/C / ethanol View Scheme

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Rx-ID: 19192489 Find similar reactions

Anand; Ranjan

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1889 - 1890 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 19194087 Find similar reactions

Multi-step reaction with 6 steps 1: 97 percent / K2CO3 / dimethylformamide / 12 h / Heating 2: 95 percent / LiAlH4 / diethyl ether 3: 93 percent / pyridinium chlorochromate, CH3COONa / CH2Cl2 / 1 h 4: 92 percent / diethyl ether / 2 h / Ambient temperature 5: p-toluenesulfonic acid / benzene / Heating 6: H2 / 10percent Pd/C / ethanol View Scheme

Anand; Ranjan

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1889 - 1890 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 8 steps 1: 84 percent / sodium hydroxide / heating 5: 28.8 g / fluoroboric acid, sodium nitrite / H2O 6: 7.6 g / warming, distillation 7: 60 percent / lithium chips / 0.5 h 8: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: 93 percent / pyridinium chlorochromate, CH3COONa / CH2Cl2 / 1 h 2: 92 percent / diethyl ether / 2 h / Ambient temperature 3: p-toluenesulfonic acid / benzene / Heating 4: H2 / 10percent Pd/C / ethanol View Scheme

Rx-ID: 19194733 Find similar reactions

Anand; Ranjan

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1889 - 1890 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 19196744 Find similar reactions

Anand; Ranjan

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1889 - 1890 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 5 steps 1: 95 percent / LiAlH4 / diethyl ether 2: 93 percent / pyridinium chlorochromate, CH3COONa / CH2Cl2 / 1 h 3: 92 percent / diethyl ether / 2 h / Ambient temperature 4: p-toluenesulfonic acid / benzene / Heating 5: H2 / 10percent Pd/C / ethanol View Scheme

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Rx-ID: 19214813 Find similar reactions

Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / benzene / Heating 2: H2 / 10percent Pd/C / ethanol View Scheme

Anand; Ranjan

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 6 p. 1889 - 1890 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 60 percent / lithium chips / 0.5 h 2: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Rx-ID: 20588066 Find similar reactions

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 20591251 Find similar reactions

Multi-step reaction with 11 steps 1: 78 percent / hydrazine hydrate / 2 h / Heating 2: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C 3: 93 percent / toluene / 2.5 h / Heating 4: 8.7 g / sodium hydroxide (20percent) / 60 °C 8: 28.8 g / fluoroboric acid, sodium nitrite / H2O 9: 7.6 g / warming, distillation 10: 60 percent / lithium chips / 0.5 h 11: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 20593284 Find similar reactions

Multi-step reaction with 5 steps 2: 28.8 g / fluoroboric acid, sodium nitrite / H2O 3: 7.6 g / warming, distillation 4: 60 percent / lithium chips / 0.5 h 5: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 9 steps 1: 93 percent / toluene / 2.5 h / Heating

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Rx-ID: 20594693 Find similar reactions

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-

2: 8.7 g / sodium hydroxide (20percent) / 60 °C 6: 28.8 g / fluoroboric acid, sodium nitrite / H2O 7: 7.6 g / warming, distillation 8: 60 percent / lithium chips / 0.5 h 9: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

1999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 20596338 Find similar reactions

Multi-step reaction with 10 steps 1: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C 2: 93 percent / toluene / 2.5 h / Heating 3: 8.7 g / sodium hydroxide (20percent) / 60 °C 7: 28.8 g / fluoroboric acid, sodium nitrite / H2O 8: 7.6 g / warming, distillation 9: 60 percent / lithium chips / 0.5 h 10: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 60 percent / lithium chips / 0.5 h 2: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Rx-ID: 20596611 Find similar reactions

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 20598278 Find similar reactions

Multi-step reaction with 3 steps 1: 7.6 g / warming, distillation 2: 60 percent / lithium chips / 0.5 h 3: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 20620918 Find similar reactions

Multi-step reaction with 4 steps 1: 28.8 g / fluoroboric acid, sodium nitrite / H2O 2: 7.6 g / warming, distillation 3: 60 percent / lithium chips / 0.5 h 4: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 8 steps 1: 8.7 g / sodium hydroxide (20percent) / 60 °C 5: 28.8 g / fluoroboric acid, sodium nitrite / H2O 6: 7.6 g / warming, distillation 7: 60 percent / lithium chips / 0.5 h 8: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

Rx-ID: 20621547 Find similar reactions

Durrani, Aziz A.; Tyman, John H. P.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 1658 - 1666 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 22224462 Find similar reactions

Multi-step reaction with 2 steps 1: palladium; aq. NaOH solution / Hydrogenation 2: aqueous NaOH View Scheme

Anker; Cook

Journal of the Chemical Society, 1945 , p. 311 Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: H2 / Pd-C 2: aq. NaOH View Scheme

Korte,F.; Sieper,H.

Justus Liebigs Annalen der Chemie, 1960 , vol. 630, p. 71 - 83 Full Text View citing articles Show Details

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Rx-ID: 22784067 Find similar reactions

Multi-step reaction with 2 steps 1: CuI 2: aq. HCl, Py View Scheme

Petrzilka,T. et al.

Helvetica Chimica Acta, 1969 , vol. 52, # 4 p. 1102 - 1134 Full Text View citing articles Show Details

Synthesize Find similar With conc. sulphuric acid in water

Hide Experimental Procedure

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Rx-ID: 25270121 Find similar reactions

Ciba-Geigy Corporation

Patent: US4020098 A1, 1977 ; Title/Abstract Full Text Show Details

2:EXAMPLE 2

EXAMPLE 2 1.0 g (0.00338 mole) of 2,4-dihydroxy-6-pentylisophthalic acid dimethyl ester is stirred in 10 ml of a mixture of conc. sulphuric acid and water (volume ratio = 5:1) until a solution is obtained, and this then heated for 4 hours in a bath at 100°. After cooling, the solution is poured on ice and extracted twice with ether (100 ml each time). The combined ethereal layers are extracted with 2 portions of 1N sodium hydroxide solution and the basic extracts acidified with hydrochloric acid; the reaction product precipitating in the form of oil is subsequently taken up in ether. The solution dried with magnesium sulphate yields, after concentration in vacuo, 481 mg of yellowish oil, which crystallises on standing. The yield of crude olivetol amounts to 79percent of theory.

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With bromine in N,N-dimethyl-formamide

T=160°C; 10 h; Cooling with ice; Hide Experimental Procedure

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Rx-ID: 38513612 Find similar reactions

FULL SPECTRUM LABORATORIES LIMITED; WINNICKI, Robert; DONSKY, Marc

Patent: WO2014/134281 A1, 2014 ; Location in patent: Paragraph 0120-0122 ; Title/Abstract Full Text Show Details

B.2:2. l-N-Pentyl-3, 5-dihydroxybenzene ( Olivetol). [0120] To a stirring ice-cooled solution of methyl 6-N-pentyl-2-hydroxy-4-oxo-cyclohex-2- ene-l-carboxylate (58.4 g, 0.24 mol) dissolved in 115 mL dimethylformamide was added dropwise 37.9 g (0.23 mol) of bromine dissolved in 60 mL of dimethylformamide. At the end of the addition (ca. 90 min) the reaction mixture was slowly heated to 80° C during which time the evolution of carbon dioxide became quite vigorous. [0121] The reaction was maintained at this temperature until gas evolution had ceased following which the reaction was further heated to 160° C and held at this temperature for approximately 10 hours. After heating, the reaction was allowed to cool and the solvent DMF was removed under reduced pressure. The residue thus obtained was treated with water (80 mL) and extracted twice with 250 mL of ether. The combined ether layers were washed with water, then washed with 2 X 80 mL of a 10percent solution of sodium bisulfite, 2 X 80 mL of a 10percent solution of acetic acid, and then again with water. [0122] After drying over anhydrous sodium sulfate the solvent was removed under reduced pressure to give 46.8 g of a viscous oil. The oil was distilled under reduced pressure to give 30.3 g (0.168 mol) (69.3percento) of olivetol as product. HPLC analysis indicated 97.5percent purity. 69.3%

With bromine in N,N-dimethyl-formamide

T=80 - 160°C; Hide Experimental Procedure

FULL SPECTRUM LABORATORIES LIMITED; DONSKY, Marc; SUN, Mingyang; PEET, Richard; WINNICKI, Robert

Patent: WO2016/30828 A1, 2016 ; Location in patent: Page/Page column 66; 67 ; Title/Abstract Full Text Show Details

B.2:2. 1-N-Pentyl-3,5-dihydroxybenzene To a stirring ice-cooled solution of methyl 6-N-pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-l- carboxylate (58.4 g, 0.24 mol) dissolved in 115 mL dimethylformamide was added dropwise 37.9 g (0.23 mol) of bromine dissolved in 60 mL of dimethylformamide. At the end of the addition (ca. 90 min) the reaction mixture was slowly heated to 80° C during which time the evolution of carbon dioxide became quite vigorous. The reaction was maintained at this temperature until gas evolution had ceased following which the reaction was further heated to 160° C and held at this temperature for approximately 10 hours. After heating, the reaction was allowed to cool and the solvent DMF was removed under reduced pressure. The residue thus obtained was treated with water (80 mL) and extracted twice with 250 mL of ether. The combined ether layers were washed with water, then washed with 2 X 80 mL of a 10percent solution of sodium bisulfite, 2 X 80 mL of a 10percent solution of acetic acid, and then again with water. After drying over anhydrous sodium sulfate the solvent was removed under reduced pressure to give 46.8 g of a viscous oil. The oil was distilled under reduced pressure to give 30.3 g (0.168 mol) (69.3percent) of olivetol as product. HPLC analysis indicated 97.5percent purity. 69.3%

With bromine in N,N-dimethyl-formamide

T=160°C; 11.5 h; Cooling with ice; Hide Experimental Procedure

Full Spectrum Laboratories Ltd; Kavarana, Malcolm J.; Peet, Richard C.

Patent: US2017/283837 A1, 2017 ; Location in patent: Paragraph 0122; 0123; 0126; 0127; 0128; 0129 ; Title/Abstract Full Text Show Details

1.B:B. 1-n-Pentyl-3,5-dihydroxybenzene (Olivetol) B. 1-n-Pentyl-3,5-dihydroxybenzene (Olivetol) (0126) (0127) To a stirring ice-cooled solution of methyl 6-N-pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate (58.4 g, 0.24 mol) dissolved in 115 mL dimethylformamide was added dropwise 37.9 g (0.23 mol) of bromine dissolved in 60 mL of dimethylformamide. At the end of the addition (ca. 90 min) the reaction mixture was slowly heated to 80° C. during which time the evolution of carbon dioxide became quite vigorous. (0128) The reaction was maintained at this temperature until gas evolution had ceased following which the reaction was further heated to 160° C. and held at this temperature for approximately 10 hours. After heating, the reaction was allowed to cool and the solvent DMF was removed under reduced pressure. The residue thus obtained was treated with water (80 mL) and extracted twice with 250 mL of ether. The combined ether layers were washed with water, then washed with 2×80 mL of a 10percent solution of sodium bisulfite, 2×80 mL of a 10percent solution of acetic acid, and then again with water. (0129) After drying over anhydrous sodium sulfate the solvent was removed under reduced pressure to give 46.8 g of viscous oil. The oil was distilled under reduced pressure to give 30.3 g (0.168 mol) (69.3percent) of olivetol as product. HPLC analysis indicated 97.5percent purity.

69.3%

With bromine in N,N-dimethyl-formamide

T=160°C; 10 h; Cooling with ice; Hide Experimental Procedure

Full Spectrum Laboratories Ltd; Peet, Richard C.; Kavarana, Malcolm J.

Patent: US2017/298399 A1, 2017 ; Location in patent: Paragraph 0189-0192 ;

Title/Abstract Full Text Show Details

A.ii:ii. 1-n-Pentyl-3,5-dihydroxybenzene (Olivetol)

To a stirring ice-cooled solution of methyl 6—N-pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate (58.4 g, 0.24 mol) dissolved in 115 mL dimethylformamide was added dropwise 37.9 g (0.23 mol) of bromine dissolved in 60 mL of dimethylformamide. At the end of the addition (ca. 90 min) the reaction mixture was slowly heated to 80° C. during which time the evolution of carbon dioxide became quite vigorous. The reaction was maintained at this temperature until gas evolution had ceased following which the reaction was further heated to 160° C. and held at this temperature for approximately 10 hours. After heating, the reaction was allowed to cool and the solvent DMF was removed under reduced pressure. The residue thus obtained was treated with water (80 mL) and extracted twice with 250 mL of ether. The combined ether layers were washed with water, then washed with 2×80 mL of a 10percent solution of sodium bisulfite, 2×80 mL of a 10percent solution of acetic acid, and then again with water After drying over anhydrous sodium sulfate the solvent was removed under reduced pressure to give 46.8 g of viscous oil. The oil was distilled under reduced pressure to give 30.3g (0.168 mol) (69.3percent) of olivetol as product. HPLC analysis indicated 97.5percent purity.

69.3%

With bromine in N,N-dimethyl-formamide

T=80 - 160°C; 11.5 h; Cooling with ice; Hide Experimental Procedure

Full Spectrum Laboratories Ltd; Peet, Richard C.; Kavarana, Malcolm J.

Patent: US2017/362195 A1, 2017 ; Location in patent: Paragraph 0133; 0134; 0135; 0136 ; Title/Abstract Full Text Show Details

I.ii:ii. 1-n-Penyl-3,5-dihydroxybenzene (Olivetol)

[0134] To a stirring ice-cooled solution of methyl 6-N-pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-l-carboxylate (58.4 g, 0.24 mol) dissolved in 115 mL dimethylformamide was added dropwise 37.9 g (0.23 mol) of bromine dissolved in 60 mL of dimethylformamide. At the end of the addition (ca. 90 min) the reaction mixture was slowly heated to 80° C. during which time the evolution of carbon dioxide became quite vigorous. [0135] The reaction was maintained at this temperature until gas evolution had ceased following which the reaction was further heated to 160° C. and held at this temperature for approximately 10 hours. After heating, the reaction was allowed to cool and the solvent DMF was removed under reduced pressure. The residue thus obtained was treated with water (80 mL) and extracted twice with 250 mL of ether. The combined ether layers were washed with water, then washed with 2*80 mL of a 10percent solution of sodium bisultite, 2*80 mL of a 10percent solution of acetic acid, and then again with water. [0136] After drying over anhydrous sodium sulfate the solvent was removed under reduced pressure to give 46.8 g of viscous oil. The oil was distilled under reduced pressure to give 30.3 g (0.168 mol) (69.3percent) of olivetol as product. HPLC analysis indicated 97.5percent purity.

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Rx-ID: 45909143 Find similar reactions

Multi-step reaction with 2 steps 1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 16 h / 110 °C / Inert atmosphere; Enzymatic reaction 2: boron tribromide / dichloromethane / 1.5 h / -15 - 20 °C / Inert atmosphere View Scheme

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas

Tetrahedron, 2017 , vol. 73, # 35 p. 5297 - 5301 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / dichloromethane / 20 - 65 °C / Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / methanol / 20 °C / 3750.38 Torr 3: boron tribromide / dichloromethane / 1.5 h / -15 - 20 °C / Inert atmosphere View Scheme

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas

Tetrahedron, 2017 , vol. 73, # 35 p. 5297 - 5301 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 45909156 Find similar reactions

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas

Tetrahedron, 2017 , vol. 73, # 35 p. 5297 - 5301 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 45909162 Find similar reactions

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas

Tetrahedron, 2017 , vol. 73, # 35 p. 5297 - 5301 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 45909178 Find similar reactions

Multi-step reaction with 2 steps 1: palladium 10 on activated carbon; hydrogen / methanol / 20 °C / 3750.38 Torr 2: boron tribromide / dichloromethane / 1.5 h / -15 - 20 °C / Inert atmosphere View Scheme

Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas

Tetrahedron, 2017 , vol. 73, # 35 p. 5297 - 5301 Title/Abstract Full Text View citing articles Show Details

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97%

With boron tribromide in dichloromethane

T=-78 - 20°C;

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Rx-ID: 2048224 Find similar reactions

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros

Journal of Labelled Compounds and Radiopharmaceuticals, 2002 , vol. 45, # 12 p. 1065 - 1076 Title/Abstract Full Text View citing articles Show Details

75%

With trimethylsilyl iodide in chloroform

T=40°C; 48 h;

Girard, Michel; Moir, David B.; Apsimon, John W.

Canadian Journal of Chemistry, 1987 , vol. 65, p. 189 - 190 Title/Abstract Full Text Show Details

With boron tribromide in dichloromethane

Pitt; Hobbs; Schran; et al.

Journal of Labelled Compounds, 1975 , vol. 11, # 4 p. 551 - 575 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 14440773 Find similar reactions

Multi-step reaction with 4 steps 1.1: magnesium turnings / diethyl ether 1.2: 88 percent / CeCl3 / tetrahydrofuran; diethyl ether / 1.5 h / -78 - 20 °C 2.1: triethylamine / tetrahydrofuran / 0.33 h 3.1: 11.92 g / lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C 4.1: 97 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros

Journal of Labelled Compounds and Radiopharmaceuticals, 2002 , vol. 45, # 12 p. 1065 - 1076 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0.33 h 2: 11.92 g / lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C 3: 97 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

Rx-ID: 14451231 Find similar reactions

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros

Journal of Labelled Compounds and Radiopharmaceuticals, 2002 , vol. 45, # 12 p. 1065 - 1076 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 14453617 Find similar reactions

Multi-step reaction with 2 steps 1: 11.92 g / lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C 2: 97 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros

Journal of Labelled Compounds and Radiopharmaceuticals, 2002 , vol. 45, # 12 p. 1065 - 1076 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 20091330 Find similar reactions

Multi-step reaction with 6 steps 1: phosphorous tribromide / CH2Cl2 / 1 h / Ambient temperature 2: 80 percent / diethyl ether / 30 h / Ambient temperature 3: 1.) borane-dimethyl sulfide complex; 2.) 3N NaOH, 30percent aqueous hydrogen peroxide / 1.) dichloromethane, 0 deg C, 25 min, then r.t., 3 h; 2.) dichloromethane, ethanol, reflux, 1 h 4: 70 percent / trimethylsilyl chloride, lithium bromide / acetonitrile / 12 h / Heating 5: 60 percent / dilithium tetrachlorocuprate / tetrahydrofuran; diethyl ether / 16 h / Ambient temperature 6: 75 percent / trimethylsilyl iodide / CHCl3 / 48 h / 40 °C View Scheme

Girard, Michel; Moir, David B.; Apsimon, John W.

Canadian Journal of Chemistry, 1987 , vol. 65, p. 189 - 190 Title/Abstract Full Text Show Details

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Rx-ID: 20092978 Find similar reactions

Multi-step reaction with 5 steps 1: 80 percent / diethyl ether / 30 h / Ambient temperature 2: 1.) borane-dimethyl sulfide complex; 2.) 3N NaOH, 30percent aqueous hydrogen peroxide / 1.) dichloromethane, 0 deg C, 25 min, then r.t., 3 h; 2.) dichloromethane, ethanol, reflux, 1 h 3: 70 percent / trimethylsilyl chloride, lithium bromide / acetonitrile / 12 h / Heating

Girard, Michel; Moir, David B.; Apsimon, John W.

Canadian Journal of Chemistry, 1987 , vol. 65, p. 189 - 190 Title/Abstract Full Text Show Details

4: 60 percent / dilithium tetrachlorocuprate / tetrahydrofuran; diethyl ether / 16 h / Ambient temperature 5: 75 percent / trimethylsilyl iodide / CHCl3 / 48 h / 40 °C View Scheme

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Rx-ID: 20094618 Find similar reactions

Multi-step reaction with 3 steps 1: 70 percent / trimethylsilyl chloride, lithium bromide / acetonitrile / 12 h / Heating 2: 60 percent / dilithium tetrachlorocuprate / tetrahydrofuran; diethyl ether / 16 h / Ambient temperature 3: 75 percent / trimethylsilyl iodide / CHCl3 / 48 h / 40 °C View Scheme

Girard, Michel; Moir, David B.; Apsimon, John W.

Canadian Journal of Chemistry, 1987 , vol. 65, p. 189 - 190 Title/Abstract Full Text Show Details

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Rx-ID: 20101089 Find similar reactions

Multi-step reaction with 7 steps 1: lithium aluminum hydride / diethyl ether / 16 h / Ambient temperature 2: phosphorous tribromide / CH2Cl2 / 1 h / Ambient temperature 3: 80 percent / diethyl ether / 30 h / Ambient temperature 4: 1.) borane-dimethyl sulfide complex; 2.) 3N NaOH, 30percent aqueous hydrogen peroxide / 1.) dichloromethane, 0 deg C, 25 min, then r.t., 3 h; 2.) dichloromethane, ethanol, reflux, 1 h 5: 70 percent / trimethylsilyl chloride, lithium bromide / acetonitrile / 12 h / Heating 6: 60 percent / dilithium tetrachlorocuprate / tetrahydrofuran; diethyl ether / 16 h / Ambient temperature 7: 75 percent / trimethylsilyl iodide / CHCl3 / 48 h / 40 °C View Scheme

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Rx-ID: 20103032

Girard, Michel; Moir, David B.; Apsimon, John W.

Canadian Journal of Chemistry, 1987 , vol. 65, p. 189 - 190 Title/Abstract Full Text Show Details

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Multi-step reaction with 4 steps 1: 1.) borane-dimethyl sulfide complex; 2.) 3N NaOH, 30percent aqueous hydrogen peroxide / 1.) dichloromethane, 0 deg C, 25 min, then r.t., 3 h; 2.) dichloromethane, ethanol, reflux, 1 h 2: 70 percent / trimethylsilyl chloride, lithium bromide / acetonitrile / 12 h / Heating 3: 60 percent / dilithium tetrachlorocuprate / tetrahydrofuran; diethyl ether / 16 h / Ambient temperature 4: 75 percent / trimethylsilyl iodide / CHCl3 / 48 h / 40 °C View Scheme

Girard, Michel; Moir, David B.; Apsimon, John W.

Canadian Journal of Chemistry, 1987 , vol. 65, p. 189 - 190 Title/Abstract Full Text Show Details

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Rx-ID: 20103191 Find similar reactions

Multi-step reaction with 2 steps 1: 60 percent / dilithium tetrachlorocuprate / tetrahydrofuran; diethyl ether / 16 h / Ambient temperature 2: 75 percent / trimethylsilyl iodide / CHCl3 / 48 h / 40 °C View Scheme

Girard, Michel; Moir, David B.; Apsimon, John W.

Canadian Journal of Chemistry, 1987 , vol. 65, p. 189 - 190 Title/Abstract Full Text Show Details

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Multi-step reaction with 3 steps 1: PBr3 / benzene 2: LiAlD4 / tetrahydrofuran / Heating 3: BBr3 / CH2Cl2

View Scheme

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Rx-ID: 22521799 Find similar reactions

Pitt; Hobbs; Schran; et al.

Journal of Labelled Compounds, 1975 , vol. 11, # 4 p. 551 - 575 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 22521807 Find similar reactions

Multi-step reaction with 2 steps 1: LiAlD4 / tetrahydrofuran / Heating 2: BBr3 / CH2Cl2

View Scheme

Pitt; Hobbs; Schran; et al.

Journal of Labelled Compounds, 1975 , vol. 11, # 4 p. 551 - 575 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 22531197 Find similar reactions

Multi-step reaction with 4 steps 1: LiAlD4 / diethyl ether 2: PBr3 / benzene 3: LiAlD4 / tetrahydrofuran / Heating 4: BBr3 / CH2Cl2

View Scheme

Pitt; Hobbs; Schran; et al.

Journal of Labelled Compounds, 1975 , vol. 11, # 4 p. 551 - 575 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 5 steps 1: H2 / Pd-C / ethanol 2: LiAlD4 / diethyl ether 3: PBr3 / benzene 4: LiAlD4 / tetrahydrofuran / Heating 5: BBr3 / CH2Cl2

View Scheme

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Rx-ID: 22532968 Find similar reactions

Pitt; Hobbs; Schran; et al.

Journal of Labelled Compounds, 1975 , vol. 11, # 4 p. 551 - 575 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 7198150 Find similar reactions

Liebman et al.

Journal of Labelled Compounds, 1971 , vol. 7, p. 241,243 Full Text Show Details

analog. mark. Dihydroolivetol (II), Quecksilberacetat.;

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Rx-ID: 7600953 Find similar reactions

Gill; Jones

Journal of Labelled Compounds, 1972 , vol. 8, p. 237,241 Full Text Show Details

3H-Dimethylolivetol, BBr3;

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96%

With boron tribromide in dichloromethane

T=-78 - 20°C; 4.75 h;

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Rx-ID: 9276410 Find similar reactions

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros

Journal of Labelled Compounds and Radiopharmaceuticals, 2002 , vol. 45, # 12 p. 1065 - 1076 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 14440777 Find similar reactions

Multi-step reaction with 4 steps 1.1: magnesium turnings / diethyl ether 1.2: 87 percent / CeCl3 / tetrahydrofuran; diethyl ether / 1.5 h / -78 - 20 °C 2.1: triethylamine / tetrahydrofuran / 0.33 h 3.1: 36.7 g / lithium triethylborohydride / tetrahydrofuran / 2.5 h / 0 - 20 °C 4.1: 96 percent / BBr3 / CH2Cl2 / 4.75 h / -78 - 20 °C View Scheme

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros

Journal of Labelled Compounds and Radiopharmaceuticals, 2002 , vol. 45, # 12 p. 1065 - 1076 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 14452511 Find similar reactions

Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0.33 h 2: 36.7 g / lithium triethylborohydride / tetrahydrofuran / 2.5 h / 0 - 20 °C 3: 96 percent / BBr3 / CH2Cl2 / 4.75 h / -78 - 20 °C View Scheme

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros

Journal of Labelled Compounds and Radiopharmaceuticals, 2002 , vol. 45, # 12 p. 1065 - 1076 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 36.7 g / lithium triethylborohydride / tetrahydrofuran / 2.5 h / 0 - 20 °C 2: 96 percent / BBr3 / CH2Cl2 / 4.75 h / -78 - 20 °C View Scheme

Rx-ID: 14454297 Find similar reactions

Nikas, Spyros P.; Thakur, Ganesh A.; Makriyannis, Alexandros

Journal of Labelled Compounds and Radiopharmaceuticals, 2002 , vol. 45, # 12 p. 1065 - 1076 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 7920432 Find similar reactions

Asahina; Fujikawa

Chemische Berichte, 1935 , vol. 68, p. 634,636, 638 Full Text View citing articles Show Details

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Rx-ID: 54990 Find similar reactions

Asahina; Asano

Chemische Berichte, 1932 , vol. 65, p. 475,581 Yakugaku Zasshi, 1932 , vol. 52, p. 417,428 Full Text View citing articles Show Details

T=150 - 200°C;

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Synthesize Find similar Rx-ID: 100151 Find similar reactions

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Asahina; Asano

Chemische Berichte, 1932 , vol. 65, p. 475,581 Yakugaku Zasshi, 1932 , vol. 52, p. 417,428

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Rx-ID: 1937272 Find similar reactions

With magnesium methanolate in methanol

1.) 1 h, 2.) room temperature, 2 d; Yield given. Yields of byproduct given;

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Jaxa-Chamiec, Albert A.; Sammes, Peter G.; Kennewell, Peter D.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (19721999), 1980 , p. 170 - 175 Title/Abstract Full Text View citing articles Show Details

Rx-ID: 31510089 Find similar reactions

Baerson, Scott R.; Pan, Zhiqiang; Rimando, Agnes M.; Dayan, Franck E.; Cook, Daniel

Patent: US2011/225676 A1, 2011 ;

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Title/Abstract Full Text Show Details

5:Polyketide Synthase Enzyme Assays

Spectral data obtained for all identified alkylresorcinolic products are provided in Table 1. Further confirmation for the formation of olivetol (AR5:0) and pentadecylresorcinol (AR15:0) in assays provided with hexanoly- and palmitoly-CoA starters was obtained by comparison of product retention times and mass spectra relative to authentic standards. GC-EI-MS: AR5:0-Rt 5.40 min, m/z 324 [M]+, m/z 309 [M-CH3]+, m/z 295 [5-propyl-1,3-phenylene)bis(oxy)bis(TMS)]+, m/z 281 [(5-ethyl-1,3-phenylene)bis(oxy)bis(TMS)]+, m/z 268 [(5-methyl-1,3-phenylene)bis(oxy)bis(TMS)]+; AR15:0-Rt 10.17 min, m/z 464 [M]+, m/z 449 [M-CH3]+, m/z 361 [449+-2(CH2)]+, m/z 361 [449+-OTMS, +H]+, m/z 323 [5-pentyl-1,3-phenylene)bis(oxy)bis(TMS)+H]+, m/z 310 [5-butyl-1,3-phenylene)bis(oxy)bis(TMS)]+, m/z 310 [5-propyl-1,3-phenylene)bis(oxy)bis(TMS)]+, m/z 281 [5-ethyl-1,3-phenylene)bis(oxy)bis(TMS)]+, m/z 268 [5-methyl-1,3-phenylene)bis(oxy)bis(TMS)]+, m/z 253 [268+-CH3]+.

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A: 32% B: 10% C: 40%

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Chandrasekharan, V.; Unnikrishnan, P.; Shah, G. D.; Bhattacharyya, S. C.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980 , vol. 19, # 12 p. 1052 - 1055 Title/Abstract Full Text Show Details

in diphenylether

heating to 155 deg C during 1 h;

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Synthesize Find similar Rx-ID: 2163466 Find similar reactions

T=160°C; 1 h; pyrolysis; rate of decarboxylation; Product distribution;

Huneck, Siegfried; Schmidt, Juergen; Tabacchi, Raffaele

Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1989 , vol. 44, # 10 p. 1283 - 1289 Title/Abstract Full Text Show Details