4-Allyl-2-methoxyphenol (Eugenol) [RRAFCDWBNXTKKO-UHFFFAOYSA-N] to Isoeugenol by Asch

Bioactivities (494)

Yield

Reactions (27)

Substances (29)

Targets (42)

Citations (57)

Conditions

References

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Rx-ID: 133204

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82%

With Grubb's 2nd generation catalyst; polydimethylsiloxane in methanol; water

T=100°C; 20 h;

Brett Runge; Mwangi, Martin T.; Bowden, Ned B.

Journal of Organometallic Chemistry, 2006 , vol. 691, # 24-25 p. 5278 - 5288 Title/Abstract Full Text View citing articles Show Details

78%

With potassium fluoride on basic alumina in ethylene glycol

T=200°C; 1.5 h;

Radhakrishna, A.S.; Suri, S.K.; Rao, K.R.K.Prasad; Sivaprakash, K.; Singh, B.B.

Synthetic Communications, 1990 , vol. 20, # 3 p. 345 - 348 Title/Abstract Full Text Show Details

With platinum on activated charcoal

T=300°C; im Kohlendioxyd-Strom;

Lewina

Zhurnal Obshchei Khimii, 1936 , vol. 6, p. 1092,1094 Chem. Zentralbl., 1937 , vol. 108, # I p. 586 Full Text View citing articles Show Details

With potassium hydroxide; diethylene glycol

T=160 - 180°C;

West

Journal of the Society of Chemical Industry, London, 1940 , vol. 59, p. 275 Full Text Show Details

Allen and Sons

Patent: GB525705 , 1939 ;

Full Text Show Details

With potassium hydroxide; glycerol

T=180°C;

Priester

Riechstoffind., 1930 , vol. 5, p. 83,108 Full Text Show Details

With potassium hydroxide; pentan-1-ol

T=140°C;

Tiemann

Chemische Berichte, 1891 , vol. 24, p. 2881 Full Text View citing articles Show Details

Haarmann; Reimer

Patent: DE57808 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 862 Full Text Show Details

With potassium hydroxide

T=130 - 140°C;

Eijkman

Chemische Berichte, 1890 , vol. 23, p. 862 Full Text View citing articles Show Details

Ciamician; Silber

Chemische Berichte, 1890 , vol. 23, p. 1165 Full Text View citing articles Show Details

Tiemann

Chemische Berichte, 1894 , vol. 27, p. 2580 Full Text View citing articles Show Details

Haarmann; Reimer

Patent: DE57808 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 862 Full Text Show Details

With pentan-1-ol; sodium

Gassmann

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1897 , vol. 124, p. 38 Full Text Show Details

With potassium hydroxide

T=220°C;

Einhorn; Frey

Chemische Berichte, 1894 , vol. 27, p. 2457 Full Text View citing articles Show Details

With potassium hydroxide; water

T=220°C; Loesen in Wasser und Ansaeuern;

Einhorn

Patent: DE76982 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 863 Full Text Show Details

Einhorn; Frey

Chemische Berichte, 1894 , vol. 27, p. 2457 Full Text View citing articles Show Details

With potassium hydroxide

beim Schmelzen;

McLang

Chem. Zentralbl., 1926 , vol. 97, # I p. 515 Full Text Show Details

McLang

Chem. Trade J., vol. 77, p. 3,180 Chem. Zentralbl., 1925 , vol. 96, # II p. 1562 Full Text Show Details

Gokhale; Sudborough; Watson

Journal of the Indian Institute of Science, 1923 , vol. 6, p. 246 Chem. Zentralbl., 1924 , vol. 95, # II p. 324 Full Text View citing articles Show Details

With potassium hydroxide; sodium hydroxide

beim Schmelzen;

McLang

Chem. Zentralbl., 1926 , vol. 97, # I p. 515 Full Text Show Details

McLang

Chem. Trade J., vol. 77, p. 3,180 Chem. Zentralbl., 1925 , vol. 96, # II p. 1562 Full Text Show Details

Gokhale; Sudborough; Watson

Journal of the Indian Institute of Science, 1923 , vol. 6, p. 246 Chem. Zentralbl., 1924 , vol. 95, # II p. 324 Full Text View citing articles Show Details

With 10 KOH/alumina

Merchan Arenas, Diego R.; Rojas Ruiz, Fernando A.; Kouznetsov, Vladimir V.

Tetrahedron Letters, 2011 , vol. 52, # 12 p. 1388 - 1391

Title/Abstract Full Text View citing articles Show Details

99 %Chromat.

With hexaaquaruthenium(II) tosylate in ethanol

T=20°C;

Kuo, Louis Y.; Delaney, Frances E.

Inorganica Chimica Acta, 2015 , vol. 435, p. 335 - 339 Title/Abstract Full Text View citing articles Show Details

With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene][2-[[(2-methylphenyl)imino]methyl]phenolyl][3-phenyl-1H-inden-1-ylidene](chloro)ruthenium(II); [Pd(µ-Br)(tBu3P)]2 in toluene

T=50°C; 1 h; Inert atmosphere;

Trita; Over; Pollini; Baader; Riegsinger; Meier; Gooßen

Green Chemistry, 2017 , vol. 19, # 13 p. 3051 - 3060 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1770372

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99%

With [CpRu(2-PiPr2-4-tBu-1-Me-imidazole)(MeCN)]PF6 in [(2)H6]acetone T=25°C; 0.0666667 h; Inert atmosphereGlovebox; Reagent/catalystTemperatureSolvent; stereoselective reaction;

Erdogan, Gulin; Grotjahn, Douglas B.

Organic Letters, 2014 , vol. 16, # 11 p. 2818 - 2821 Title/Abstract Full Text View citing articles Show Details

96%

With platinum(II) chloride in methanol

Zhao, Huiping; Brandt, Gary E.; Galam, Lakshmi; Matts, Robert L.; Blagg, Brian S.J.

Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 9 p. 2659 - 2664 Title/Abstract Full Text View citing articles Show Details

95.9%

With [CpRu(2-PiPr2-4-tBu-1-Me-imidazole)(MeCN)]PF6

T=20°C; 0.333333 h; GloveboxInert atmosphereGreen chemistry; Catalytic behavior; Reagent/catalyst; diastereoselective reaction; Hide Experimental Procedure

Larsen, Casey R.; Paulson, Erik R.; Erdogan, Gulin; Grotjahn, Douglas B.

Synlett, 2015 , vol. 26, # 17 art. no. ST-2015-B0231-L, p. 2462 - 2466 Title/Abstract Full Text View citing articles Show Details

Eugenol to (E)-Isoeugenol

In a glove box, a 50 mL round bottomed flask equipped with a magnetic stir bar was added eugenol (16.43 g, 0.1 mol), capped with a rubber septum, and removed from the glove box. In an inert atmosphere glove box, catalyst 1(60.5 mg, 0.101 mmol, 0.1 molpercent) was measured into a scintillation vial, capped, and brought out of the glove box. The septum was removed from the reaction flask and thecatalyst was quickly added, followed by bubbling nitrogen through the liquid to remove any air that had entered. Aliquots (ca. 5 μL) were removed from the reaction at 5, 10,and 20 minutes using a gastight syringe and analyzed by 1H NMR for completion. Full conversion of eugenol to (E)-isoeugenol occurred after 20 minutes, and the product was isolated by vacuum distillation (2 torr, 98 oC) to afford 15.76 g (95.9percent) of (E)-isoeugenolas a clear, colorless oil. To accurately determine amount of starting material remaining,105.1 mg of the distillate was weighed out in an NMR tube containing 0.5-0.7 mL CDCl3and analyzed by 1H NMR; percentages were calculated assuming a two-component mixture (eugenol/isoeugenol), using residual chloroform peak as internal standard. Peaks used: eugenol 5.11 ppm (2H), 3.34 ppm (2H); isoeugenol 6.36 ppm (1H), 6.12 ppm (1H), 1.90 ppm (3H).

90%

With palladium dichloride in methanol

24 h; Inert atmosphere;

Nielsen, Alex J.; Jenkins, Hilary A.; McNulty, James

Chemistry - A European Journal, 2016 , vol. 22, # 27 p. 9111 - 9115 Title/Abstract Full Text View citing articles Show Details

86%

With C21H35N3PRu*F6P(1-) T=20°C; Inert atmosphereneat (no solvent); stereoselective reaction;

Larsen, Casey R.; Grotjahn, Douglas B.

Journal of the American Chemical Society, 2012 , vol. 134, # 25 p. 10357 - 10360 Title/Abstract Full Text View citing articles Show Details

85%

With palladium dichloride in methanol

T=20°C; 24 h;

Curti, Claudio; Zanardi, Franca; Battistini, Lucia; Sartori, Andrea; Rassu, Gloria; Pinna, Luigi; Casiraghi, Giovanni

Journal of Organic Chemistry, 2006 , vol. 71, # 22 p. 8552 - 8558 Title/Abstract Full Text View citing articles Show Details

81%

With di-μ-bromobis(tri-tertbutylphosphine)dipalladium(I) in toluene

T=50°C; 2 h; Inert atmosphere; optical yield given as percent de;

Mamone, Patrizia; Gruenberg, Matthias F.; Fromm, Andreas; Khan, Bilal A.; Goossen, Lukas J.

Organic Letters, 2012 , vol. 14, # 14 p. 3716 - 3719 Title/Abstract Full Text View citing articles Show Details

22%

With [Ru(η5-C5Me5)(CH3CN){P(OEt)3}2]BPh4 in water T=95°C; 18 h;

Sperni, Laura; Scarso, Alessandro; Strukul, Giorgio

Inorganica Chimica Acta, 2017 , vol. 455, p. 535 - 539

Title/Abstract Full Text View citing articles Show Details

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2.3. Catalytic procedure

General procedure: In a 3 mL vial were introduced the surfactant followed by water(1 mL). The mixture was stirred until complete dissolution and formation of a clear solution. To this, catalyst 1 (0.005 mmol) was added and the mixture was stirred for 10 min, followed by allylbenzene(50 eq. with respect to 1). The mixture was heated at 95 C under stirring at 750 rpm. After 18 h the aqueous reaction mixture was extracted two times with ethyl acetate and the organic phase was analyzed by GC and GC–MS. The structure ofthe isomerized products were confirmed by GC–MS and 1H NMR. 15%

With C44H58Cl2N4Pd in methanol; toluene

T=20°C; 3 h;

Spallek, Markus J.; Stockinger, Skrollan; Goddard, Richard; Trapp, Oliver

Advanced Synthesis and Catalysis, 2012 , vol. 354, # 8 p. 1466 - 1480 Title/Abstract Full Text View citing articles Show Details

99 % Spectr.

With hexaaquaruthenium(II) in ethanol-d6; water-d2

T=24.9°C; 24 h; ΔH(excit.), ΔS(excit.); Thermodynamic dataRate constant;

Karlen, Thomas; Ludi, Andreas

Helvetica Chimica Acta, 1992 , vol. 75, # 5 p. 1604 - 1606 Title/Abstract Full Text Show Details

99 % Spectr.

With hexaaquaruthenium(II) in ethanol-d6; water-d2

T=24.9°C; 24 h;

Karlen, Thomas; Ludi, Andreas

Helvetica Chimica Acta, 1992 , vol. 75, # 5 p. 1604 - 1606 Title/Abstract Full Text Show Details

With H2 activated polymer-supported (pC6H4-PPh2)2Ir(+)(COD)PF6(-); hydrogen in tetrahydrofuran

T=20°C; 24 h;

Lee, Ai-Lan; Ley, Steven V

Organic and biomolecular chemistry, 2003 , vol. 1, # 22 p. 3957 - 3966 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 90 percent / Ag2O / CCl4 / 65 °C 2: NaBH4 / CCl4; methanol / Ambient temperature View Scheme

Zanarotti, Antonio

Journal of Organic Chemistry, 1985 , vol. 50, # 7 p. 941 - 945 Title/Abstract Full Text View citing articles Show Details

With RuCl2(η6-C6H5OCH2CH2OH){P(Ph)3} in ethanol T=80°C; 0.666667 h; Inert atmosphere; Reagent/catalystpH-valueSolvent; diastereoselective reaction;

Lastra-Barreira, Beatriz; Diaz-Alvarez, Alba E.; Menendez-Rodriguez, Lucia; Crochet, Pascale

RSC Advances, 2013 , vol. 3, # 43 p. 19985 - 19990 Title/Abstract Full Text View citing articles Show Details

With [CpRu(PN)(MeCN)]PF6 in toluene

T=20°C; 0.5 h; Inert atmosphereGlovebox; diastereoselective reaction;

Higman, Carolyn S.; De Araujo; Fogg, Deryn E.

Catalysis Science and Technology, 2016 , vol. 6, # 7 p. 2077 - 2084 Title/Abstract Full Text View citing articles Show Details

With palladium (II) acetate; bis(pinacol)diborane; tricyclohexylphosphine in toluene

T=80°C; 12 h; Sealed tubeInert atmosphere;

Ojha, Devi Prasan; Gadde, Karthik; Prabhu, Kandikere Ramaiah

Journal of Organic Chemistry, 2017 , vol. 82, # 9 p. 4859 - 4865 Title/Abstract Full Text View citing articles Show Details

100 %Chromat.

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With potassium fluoride on basic alumina in ethylene glycol

0.15 h; Neat (no solvent)Microwave irradiation; optical yield given as percent de;

Luu, Thi Xuan Thi; Lam, Trinh To; Le, Thach Ngoc; Duus, Fritz

Molecules, 2009 , vol. 14, # 9 p. 3411 - 3424 Title/Abstract Full Text View citing articles Show Details

With tri-tert-butyl phosphine; isobutyryl chloride; bis(dibenzylideneacetone)-palladium(0) in toluene

Gauthier, Delphine; Lindhardt, Anders T.; Olsen, Esben P. K.; Overgaard, Jacob; Skrydstrup, Troels

T=80°C; 24 h; Inert atmosphere; optical yield given as percent destereoselective reaction;

Journal of the American Chemical Society, 2010 , vol. 132, # 23 p. 7998 - 8009 Title/Abstract Full Text View citing articles Show Details

With ruthenium containing hydrotalcite T=210°C; 2 h; Inert atmosphere; optical yield given as percent de;

Sharma, Sumeet K.; Parikh, Parimal A.; Jasra, Raksh V.

Journal of Molecular Catalysis A: Chemical, 2010 , vol. 317, # 1-2 p. 27 - 33 Title/Abstract Full Text View citing articles Show Details

With [(dppb)Pt(C6F5)(H2O)]OTf in chloroform

T=50°C; 24 h; optical yield given as percent dediastereoselective reaction;

Scarso, Alessandro; Colladon, Marco; Sgarbossa, Paolo; Santo, Claudio; Michelin, Rino A.; Strukul, Giorgio

Organometallics, 2010 , vol. 29, # 6 p. 1487 - 1497 Title/Abstract Full Text View citing articles Show Details

With RuCl2(η6-C6H5OCH2CH2OH){P(OEt)3} in ethanol T=80°C; 6 h; Inert atmosphere; Reagent/catalystpH-valueSolvent; diastereoselective reaction;

Lastra-Barreira, Beatriz; Diaz-Alvarez, Alba E.; Menendez-Rodriguez, Lucia; Crochet, Pascale

RSC Advances, 2013 , vol. 3, # 43 p. 19985 - 19990 Title/Abstract Full Text View citing articles Show Details

With C51H41P2Ru(1+)*C32H12BF24(1-) in neat (no solvent) T=110°C; 16 h; Sealed tube; stereoselective reaction;

Manzini, Simone; Nelson, David J.; Nolan, Steven P.

ChemCatChem, 2013 , vol. 5, # 10 p. 2848 - 2851 Title/Abstract Full Text View citing articles Show Details

With aluminium(III) triflate; palladium diacetate

T=30°C; 4 h; Reagent/catalyst;

Senan, Ahmed M.; Qin, Shuhao; Zhang, Sicheng; Lou, Chenling; Chen, Zhuqi; Liao, Rong-Zhen; Yin, Guochuan

ACS Catalysis, 2016 , vol. 6, # 7 p. 4144 - 4148 Title/Abstract Full Text View citing articles Show Details

With pentylene glycol; potassium hydoxide in toluene

T=50 - 165°C; 8 h; Inert atmosphereIndustrial scale; Hide Experimental Procedure

Chongqing Xinxiang Xiangrong Fine Chemical Co., Ltd; Zhao, Huawen; Ji, Weigang; Gan, Jianqiang; Tang, Ling; Hong, Wei

Patent: CN103408407 B, 2016 ; Location in patent: Paragraph 0049; 0050; 0051; 0052; 0053; 0054; 0055-0058 ; Title/Abstract Full Text Show Details

2:Method for synthesizing isoeugenol

A three-necked flask were successively added 70.0 g of 1,2-propanediol, 26.0 g of potassium hydroxide, stir mixing, 30.0 g of eugenol was added under nitrogen, and stirring was continued mixing;. B The reaction was placed under nitrogen over 20 minutes to quickly warmed to 165 , reflux for 8 hours, the reaction was blocking reaction;. C cooled to 50-60 , acidified with 50percent sulfuric acid was added to a solution of pH = 3 ~ 4;. D was added 200 ml of toluene was stirred uniformly, filtered and the solid washed with a small amount of toluene;. E The filtrate was allowed to stand, the organic phase was separated, the aqueous phase was extracted with toluene, and the combined organic phase;f. washing the organic phase with water to neutral, toluene was removed by rotary evaporator, vested crude, the crude vacuum distillation to obtain the product.g. Connect steps e and f in the aqueous phases were combined, neutralized potassium hydroxide, the water was distilled off at atmospheric pressure, and then distilled under reduced pressure to recover the solvent.Product quality: 25.5 g.2, the products were determined by gas content of 99.45percent, which cis-isoeugenol accounted for 8.14percent, trans-isoeugenol accounted for 91.31percent. With palladium (II) acetate; water; bis(pinacol)diborane; PCy3 in toluene

T=20°C; 12 h; Sealed tubeInert atmosphere;

Ojha, Devi Prasan; Gadde, Karthik; Prabhu, Kandikere Ramaiah

Journal of Organic Chemistry, 2017 , vol. 82, # 9 p. 4859 - 4865 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 45315026

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A: 25 %Spectr. B: 72%

With trimethylaluminum; cesium fluoride; (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane; cobalt acetylacetonate in N,N-dimethyl acetamide; toluene

T=60°C; P=760.051 Torr; 12 h; Inert atmosphereSealed tube; regioselective reaction;

Michigami, Kenichi; Mita, Tsuyoshi; Sato, Yoshihiro

Journal of the American Chemical Society, 2017 , vol. 139, # 17 p. 6094 - 6097 Title/Abstract Full Text View citing articles Show Details

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A: 64 %Chromat. B: 24 %Chromat. C: 10 %Chromat.

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With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro[[2-(1-methyl-2-oxopropoxy)phenyl]methylene]ruthenium(II); [Pd(µ-Br)(tBu3P)]2 in dichloromethane

T=50°C; 1 h; Inert atmosphere;

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Trita; Over; Pollini; Baader; Riegsinger; Meier; Gooßen

Green Chemistry, 2017 , vol. 19, # 13 p. 3051 - 3060 Title/Abstract Full Text View citing articles Show Details

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A: 90 %Chromat. B: 5 %Chromat.

With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro[[2-(1-methyl-2-oxopropoxy)phenyl]methylene]ruthenium(II); [Pd(µ-Br)(tBu3P)]2 in tetrahydrofuran

T=50°C; 1 h; Inert atmosphere;

Trita; Over; Pollini; Baader; Riegsinger; Meier; Gooßen

Green Chemistry, 2017 , vol. 19, # 13 p. 3051 - 3060 Title/Abstract Full Text View citing articles Show Details

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A: 35

With hydrogen in methanol

Petitjean, Laurene; Gagne, Raphael; Beach, Evan S.; Xiao, Dequan; Anastas, Paul T.

%Spectr.

T=180°C; P=30003 Torr; 18 h; Sealed tube;

Green Chemistry, 2016 , vol. 18, # 1 p. 150 - 156 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 39885845

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With methoxy(cyclooctadiene)rhodium(I) dimer; trisodium tris(3-sulfophenyl)phosphine; hydrogen; cetyltrimethylammonim bromide in water

T=100°C; P=15001.5 Torr; 1 h; AutoclaveSchlenk techniqueInert atmosphere; Catalytic behaviorKinetics; PressureSolventTemperatureReagent/catalyst; regioselective reaction; Hide Experimental Procedure

Baricelli, Pablo J.; Rodriguez, Mariandry; Melean, Luis G.; Alonso, Maria Modroño; Borusiak, Margarita; Rosales, Merlin; Gonzalez, Beatriz; De Oliveira, Kelley C. B.; Gusevskaya, Elena V.; Dos Santos, Eduardo N.

Applied Catalysis A: General, 2015 , vol. 490, p. 163 - 169 Title/Abstract Full Text View citing articles Show Details

2.2. Catalytic runs

General procedure: The catalytic runs were performed in a mechanically stirredstainless steel Parr 4560 bomb coupled with a 4282 control mod-ule with a PDI temperature controller, tachometer, and a pressuretransducer connected to a field logger apparatus. In a typical exper-iment the catalyst precursor [Rh(COD)(-OMe)]2(2.5 × 10−6mol),TPPTS (5.0 × 10−5mol) and the phase transfer agent cetyltrimethy-lammonium bromide (CTAB, 0.0–2.0 × 10−4mol) were dissolvedin 20 mL of deoxygenated water in a Schlenk tube under argon.The solution was transferred into the bomb, and the substrate(1.0–2.0 × 10−2mol) was placed in a pressureequalized reservoiron the top of the bomb. The reactor was pressurized with thedesired carbon monoxide pressure (5–20 bar) and then with hydro-gen (5–20 bar) up to the desired total pressure. The bomb washeated to the desired temperature (80–120C) and kept for onehour under mechanical stirring (750 rpm). The substrate was thenadded and the register of the syngas pressure drop was initiated.After pressure drop stopped, the reactor was cooled, vented, theorganic phase was extracted with toluene (20 mL) and analysed by GC. A

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Rx-ID: 32101448

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A: 6 %Chromat. B: 32 %Chromat. C: 62 %Chromat.

With C44H34N4O8P2Rh2S2(2-)*2Na(1+); hydrogen; cetyltrimethylammonium chloride in water; toluene T=80°C; P=15526.6 Torr; 8 h; chemoselective reaction;

Melean, Luis G.; Rodriguez, Mariandry; Romero, Marynell; Alvarado, Maria L.; Rosales, Merlin; Baricelli, Pablo J.

Applied Catalysis A: General, 2011 , vol. 394, # 1-2 p. 117 - 123 Title/Abstract Full Text View citing articles Show Details

A: 6 %Chromat. B: 62 %Chromat. C: 31 %Chromat.

With C44H34N4O8P2Rh2S2(2-)*2Na(1+); hydrogen; cetyltrimethylammonium chloride in water; toluene T=80°C; P=15526.6 Torr; 3 h; chemoselective reaction;

Melean, Luis G.; Rodriguez, Mariandry; Romero, Marynell; Alvarado, Maria L.; Rosales, Merlin; Baricelli, Pablo J.

Applied Catalysis A: General, 2011 , vol. 394, # 1-2 p. 117 - 123 Title/Abstract Full Text View citing articles Show Details

With hydrogen in toluene

T=70°C; P=45603.1 Torr; 17 h; Inert atmosphereSchlenk technique; Catalytic behavior; Pressure; Hide Experimental Procedure

Carvalho, Glenda A.; Gusevskaya, Elena V.; Santos, Eduardo N. Dos

Journal of the Brazilian Chemical Society, 2014 , vol. 25, # 12 p. 2370 - 2377 Title/Abstract Full Text View citing articles Show Details

Catalytic runs

General procedure: A mechanically stirred stainless steel Parr 4560 bomb coupled with a 4282 control module with a PID temperature controller and tachometer was employed as the reaction vessel. The bomb was loaded with the solid catalyst and three cycles of vacuum/argon were made. The solvent (15 mL) and the substrate (5 mmol) were introduced with a syringe through a valved port under argon. The vessel was pressurized with carbon monoxide followed by hydrogen up to the reported pressure. Stirring and heating were then started, and the desired temperature was attained in about 5 min. At appropriate time intervals, stirring was stopped and liquid samples were taken through a valved dip tube after quick catalyst settling. Recycling experiments were performed maintaining the catalyst in the vessel and washing it with the same solvent employed in the reaction before a new cycle to remove product residues. A

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A: 11 %Chromat. B: 13 %Chromat. C: 59 %Chromat. D: 4 %Chromat. E: 1 %Chromat.

With Rh/Al2O3; hydrogen in α-n-hexadecene

T=249.84°C; P=22502.3 Torr; 6 h;

Deepa, Ayillath K.; Dhepe, Paresh L.

ChemPlusChem, 2014 , vol. 79, # 11 p. 1573 - 1583 Title/Abstract Full Text View citing articles Show Details

A: 10 %Chromat. B: 3 %Chromat. C: 44 %Chromat. D: 15 %Chromat. E: 3 %Chromat.

With hydrogen in α-n-hexadecene

T=249.84°C; P=22502.3 Torr; 6 h;

Deepa, Ayillath K.; Dhepe, Paresh L.

ChemPlusChem, 2014 , vol. 79, # 11 p. 1573 - 1583 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 34577049

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With methoxy(cyclooctadiene)rhodium(I) dimer; trifluorormethanesulfonic acid; hydrogen; triphenylphosphine in toluene

T=120°C; P=30003 Torr; 24 h; Hide Experimental Procedure

Oliveira, Kelley C.B.; Santos, Alexandra G.; Dos Santos

Applied Catalysis A: General, 2012 , vol. 445-446, p. 204 - 208 Title/Abstract Full Text View citing articles Show Details

2.2 Catalytic runs#10;

The pre-catalyst [Rh(cod)(μ-OMe)]2 (5.0 × 10−3 mmol), the phosphorus ancillary (if any) and a PTFE-covered magnetic stirring bar were placed in a stainless steel bomb, which was closed and purged with three cycles of vacuum and argon. In a Schlenk tube, a solution was prepared by adding toluene (30 mL), eugenol (10 mmol), di-n-butylamine (10 mmol) and then the acid (if any). The solution was transferred under inert atmosphere to the bomb, which was pressurized with carbon monoxide (10–20 atm) and then with hydrogen (to 40–80 atm). The bomb was placed in a pre-heated silicone bath over magnetic stirring. Liquid samples were taken periodically through a dip tube.

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Rx-ID: 34577050

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With methoxy(cyclooctadiene)rhodium(I) dimer; sulfuric acid; hydrogen; triphenylphosphine in toluene

T=120°C; P=30003 Torr; 24 h; Hide Experimental Procedure

Oliveira, Kelley C.B.; Santos, Alexandra G.; Dos Santos

Applied Catalysis A: General, 2012 , vol. 445-446, p. 204 - 208 Title/Abstract Full Text View citing articles Show Details

2.2 Catalytic runs

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Rx-ID: 32101446

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A: 7 %Chromat. B: 13 %Chromat. C: 32 %Chromat. D: 48 %Chromat.

With BF4(1-)*C57H46NO10P3RuS3(2-)*3Na(1+); hydrogen; cetyltrimethylammonium chloride in water; toluene T=100°C; P=46579.7 Torr; 10 h; chemoselective reaction;

Melean, Luis G.; Rodriguez, Mariandry; Romero, Marynell; Alvarado, Maria L.; Rosales, Merlin; Baricelli, Pablo J.

Applied Catalysis A: General, 2011 , vol. 394, # 1-2 p. 117 - 123 Title/Abstract Full Text View citing articles Show Details

A: 19 %Chromat. B: 40 %Chromat. C: 27 %Chromat. D: 14 %Chromat.

With C44H34N4O8P2Rh2S2(2-)*2Na(1+); hydrogen in water; toluene T=80°C; P=11401.1 Torr; 3 h; chemoselective reaction;

Melean, Luis G.; Rodriguez, Mariandry; Romero, Marynell; Alvarado, Maria L.; Rosales, Merlin; Baricelli, Pablo J.

Applied Catalysis A: General, 2011 , vol. 394, # 1-2 p. 117 - 123 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 29466869

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A: 21 %Chromat. B: 60%

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With [rhodium(I)(carbonyl)2(acetylacetonate)]; phosphoric acid; hydrogen; methoxybenzene; triphenylphosphine in dichloromethane

T=110°C; P=15514.9 Torr; 2 h; Autoclave;

Alhaffar, Mouheddin; Suleiman, Rami; Ali, Bassam El

Catalysis Communications, 2010 , vol. 11, # 8 p. 778 - 782 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 24877165

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With hydrogen; rhodium(II)bis(2-ethylhexanoate) in water; toluene

T=125°C; P=18751.9 Torr; 10 h;

Celanese Chemicals Europe GmbH

Patent: EP1719752 A1, 2006 ; Location in patent: Page/Page column 6 ; Title/Abstract Full Text Show Details

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Rx-ID: 1770369

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With potassium hydroxide; Aliquat

0.2 h; Irradiationother basic system, other additives, var. microwave power and time; Product distribution;

Loupy; Le Ngoc

Synthetic Communications, 1993 , vol. 23, # 18 p. 2571 - 2577 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 25462627

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Rhone-Poulenc S. A.

Patent: US4138411 A1, 1979 ;

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Title/Abstract Full Text Show Details

2:EXAMPLE 2

EXAMPLE 2 A mixture of 200 g. of eugenol and 10 mg. of Ru3 (CO)12 (i.e. 0.0023percent of elementary ruthenium) is heated to 130° C. for 1 hour 55 minutes. By distilling the reaction mass, 198 g. of isoeugenol are recovered. The yield based on the eugenol used is 99percent (conversion rate 100percent). A

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Synthesize Find similar Rx-ID: 25462628

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B: 85.2%

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Rhone-Poulenc S. A.

Patent: US4138411 A1, 1979 ; Title/Abstract Full Text Show Details

16:EXAMPLE 16

EXAMPLE 16 A mixture of 73 g. of eugenol and 5.7 mg. of osmium trichloride is brought for 4 hours 25 minutes to 130° C. After distillation, 65.2 g. of a mixture, containing (as measured by gas-liquid chromatography) 13.8percent of eugenol, 6.8percent of cis-isoeugenol and 79.4percent of trans-isoeugenol are obtained. The conversion rate is 88percent and the yield is 85.2percent, based on the converted eugenol.

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Rx-ID: 7161289

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With potassium hydroxide; paraffin oil

T=244°C;

Jemac A.G.

Patent: CH175671 , 1934 ; Full Text Show Details

With potassium hydroxide; phenol

T=150 - 170°C;

Verona Chem. Co.

Patent: US1787036 , 1928 ; Full Text Show Details

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Rx-ID: 7161290

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With potassium hydroxide; paraffin oil

T=244°C;

Jemac A.G.

Patent: CH175671 , 1934 ; Full Text Show Details

With potassium hydroxide; phenol

T=150 - 170°C;

Verona Chem. Co.

Patent: US1787036 , 1928 ; Full Text Show Details

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Rx-ID: 6675068

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Gokhale; Sudborough; Watson

Journal of the Indian Institute of Science, 1923 , vol. 6, p. 246 Chem. Zentralbl., 1924 , vol. 95, # II p. 324 Full Text View citing articles Show Details

durch Schmelzen;

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Rx-ID: 6675071

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Gokhale; Sudborough; Watson

Journal of the Indian Institute of Science, 1923 , vol. 6, p. 246 Chem. Zentralbl., 1924 , vol. 95, # II p. 324 Full Text View citing articles Show Details

durch Schmelzen;

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Rx-ID: 6675070

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Graebe; Kraft

Chemische Berichte, 1906 , vol. 39, p. 799 Full Text Show Details

beim Verschmelzen;

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Rx-ID: 6675072

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Gassmann

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1897 , vol. 124, p. 38 Full Text Show Details

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Rx-ID: 6675066

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Eijkman

Chemische Berichte, 1890 , vol. 23, p. 862 Full Text View citing articles Show Details

Ciamician; Silber

Chemische Berichte, 1890 , vol. 23, p. 1165 Full Text View citing articles Show Details

Tiemann

Chemische Berichte, 1894 , vol. 27, p. 2580 Full Text View citing articles Show Details

Haarmann and Reimer

Patent: DE57808 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 862 Full Text Show Details

T=130 - 140°C; unter Druck;

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Rx-ID: 6675067

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T=200 - 230°C; beim Schmelzen;

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Einhorn

Patent: DE76982 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 863 Full Text Show Details

Einhorn; Frey

Chemische Berichte, 1894 , vol. 27, p. 2457 Full Text View citing articles Show Details

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Rx-ID: 6675069

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T=140°C;

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Tiemann

Chemische Berichte, 1891 , vol. 24, p. 2881 Full Text View citing articles Show Details

Haarmann and Reimer

Patent: DE57808 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 862 Full Text Show Details