Reaxys
PubChem
eMolecules
Reactions (62)
Yield
LabNetwork
Substances (12)
Citations (69)
Conditions
References
1
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2
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Rx-ID: 315699 Find similar reactions
With 1-iso-propyl-4-methylbenzene; sodium
T=160°C;
Karrer; Alagil
Helvetica Chimica Acta, 1947 , vol. 30, p. 1777 Full Text View citing articles Show Details
With xylene; sodium t-butanolate
Erhitzen des jeweiligen Reaktionsprodukts mit wss. Schwefelsaeure oder Salzsaeure;
Parker et al.
Journal of the Chemical Society, 1959 , p. 2433,2436 Full Text View citing articles Show Details
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Rx-ID: 744897 Find similar reactions
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With water
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Robinson
Journal of the Chemical Society, 1917 , vol. 111, p. 766 Full Text View citing articles Show Details
3
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Rx-ID: 764796 Find similar reactions
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Robinson
Journal of the Chemical Society, 1917 , vol. 111, p. 766 Full Text View citing articles Show Details
Erhitzen der sauren Loesung des Reaktionsprodukts;
4
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Rx-ID: 771096 Find similar reactions
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in verduennter waessriger Loesung im pH-Bereich 3-11 bei ca. 3-taegiem Stehenlassen bei Raumtemperatur;
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Keagle; Hartung
Journal of the American Chemical Society, 1946 , vol. 68, p. 1608 Full Text View citing articles Show Details
Schoepf; Lehmann
Justus Liebigs Annalen der Chemie, 1935 , vol. 518, p. 1,25 Full Text View citing articles Show Details
Schoepf; Lehmann
Justus Liebigs Annalen der Chemie, 1935 , vol. 518, p. 1,25 Full Text View citing articles Show Details
T=20 - 25°C; bei pH 3-11;
5
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Rx-ID: 804921 Find similar reactions
Merck
Patent: DE118607 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1146 Full Text Show Details
elektrolytischen Oxydation in saurer oder swach alkalischer Loesung;
6
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Rx-ID: 805045 Find similar reactions
With chromium(III) oxide; sulfuric acid
T=0°C;
Polonovski; Polonovski
Bulletin de la Societe Chimique de France, 1927 , vol. <4>41, p. 1187,1188 Full Text View citing articles Show Details
With chromic acid; acetic acid
T=60 - 70°C;
Willstaetter
Patent: DE89597 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 1212 Full Text Show Details
Willstaetter
Chemische Berichte, 1896 , vol. 29, p. 396,947 Full Text View citing articles Show Details
With sulfuric acid; chromic acid
T=50 - 55°C;
Ciamician; Silber
Chemische Berichte, 1896 , vol. 29, p. 490 Gazzetta Chimica Italiana, 1896 , vol. 26 II, p. 161 Full Text View citing articles Show Details
With sulfuric acid; permanganate(VII) ion
T=10 - 12°C;
Merck
Patent: DE117628 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1144 Full Text Show Details
Willstaetter
Chemische Berichte, 1900 , vol. 33, p. 1163 Justus Liebigs Annalen der Chemie, 1903 , vol. 326, p. 101
Full Text View citing articles Show Details
With lead dioxide
T=60 - 70°C;
Merck
Patent: DE117629 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1145 Full Text Show Details
Willstaetter
Chemische Berichte, 1900 , vol. 33, p. 1163 Justus Liebigs Annalen der Chemie, 1903 , vol. 326, p. 101 Full Text View citing articles Show Details
With potassium hexacyanoferrate(III)
Merck
Patent: DE117630 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1145 Full Text Show Details
With sulfuric acid
elektrolytische Oxydation, an einer Bleianode;
Merck
Patent: DE128855 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1150 Full Text Show Details
Merck
Patent: DE118607 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1146 Full Text Show Details
With ammonium sulfate
elektrolytische Oxydation, an einer Bleianode;
Merck
Patent: DE128855 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1150 Full Text Show Details
Merck
Patent: DE118607 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1146 Full Text Show Details
With chlorobenzene; sodium t-butanolate; CyJohnPhos; bis(dibenzylideneacetone)-palladium(0) in toluene
T=105°C; 6 h;
Bei, Xiaohong; Hagemeyer, Alfred; Volpe, Anthony; Saxton, Robert; Turner, Howard; Guram, Anil S.
Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8626 - 8633 Title/Abstract Full Text View citing articles Show Details
7
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Rx-ID: 805085 Find similar reactions
With chromic acid; acetic acid
T=60 - 70°C;
Willstaetter
Patent: DE89597 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 1212 Full Text Show Details
Willstaetter
Chemische Berichte, 1896 , vol. 29, p. 396,947 Full Text View citing articles Show Details
With sulfuric acid; permanganate(VII) ion
T=10 - 12°C;
Merck
Patent: DE117628 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1144 Full Text Show Details
Willstaetter
Chemische Berichte, 1900 , vol. 33, p. 1163 Justus Liebigs Annalen der Chemie, 1903 , vol. 326, p. 101 Full Text View citing articles Show Details
With lead dioxide
T=60 - 70°C;
Merck
Patent: DE117629 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1145 Full Text Show Details
Willstaetter
Chemische Berichte, 1900 , vol. 33, p. 1163 Justus Liebigs Annalen der Chemie, 1903 , vol. 326, p. 101 Full Text View citing articles Show Details
With potassium hexacyanoferrate(III)
Merck
Patent: DE117630 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1145 Full Text Show Details
8
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Rx-ID: 810106 Find similar reactions
With sulfuric acid; chromic acid
T=60°C; und anschliessendem Kochen mit Schwefelsaeure;
Willstaetter; Bode
Chemische Berichte, 1900 , vol. 33, p. 414 Full Text View citing articles Show Details
Willstaetter; Mueller,W.
Chemische Berichte, 1898 , vol. 31, p. 2660 Full Text View citing articles Show Details
A
B
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9
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A: 12% B: 25%
With mercury(II) diacetate in acetic acid
18 h; Heating;
Leete, Edward; Kim, Sung Hoon
Journal of the Chemical Society, Chemical Communications, 1989 , # 24 p. 1899 - 1900 Title/Abstract Full Text View citing articles Show Details
10
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Rx-ID: 2437215 Find similar reactions
Sarel, Shalom; Dykman, Edmund
Heterocycles, 1981 , vol. 15, # 2 p. 719 - 734 Title/Abstract Full Text Show Details
With K2CO3,H2/Ra Ni 28 in water
P=3.3 Torr; 0.5 h;
11
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Rx-ID: 3477975 Find similar reactions
With sulfuric acid
Ambient temperature; Yield given;
Moriarty, Robert M.; Prakash, Om; Vavilikolanu, Pushra R.
Synthetic Communications, 1986 , vol. 16, # 10 p. 1247 - 1254 Title/Abstract Full Text Show Details
in dichloromethane
Ambient temperaturealso on treatment with dilute H2SO4; Product distribution;
Moriarty, Robert M.; Prakash, Om; Vavilikolanu, Pushra R.
Synthetic Communications, 1986 , vol. 16, # 10 p. 1247 - 1254 Title/Abstract Full Text Show Details
12
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P=3.3 Torr; 0.5 h;
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Rx-ID: 3600949 Find similar reactions
Sarel, Shalom; Dykman, Edmund
Heterocycles, 1981 , vol. 15, # 2 p. 719 - 734 Title/Abstract Full Text Show Details
13
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Rx-ID: 3634452 Find similar reactions
With nickel in ethyl acetate
4 h; Ambient temperature;
Pandey; Lakshmaiah; Ghatak
Tetrahedron Letters, 1993 , vol. 34, # 45 p. 7301 - 7304 Title/Abstract Full Text View citing articles Show Details
14
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Rx-ID: 3731931 Find similar reactions
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Lansbury, Peter T.; Spagnuolo, Ciro J.; Grimm, Erich L.
Tetrahedron Letters, 1990 , vol. 31, # 28 p. 3965 - 3968 Title/Abstract Full Text View citing articles Show Details
in methanol; water
Yield given;
15
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Rx-ID: 3747427 Find similar reactions
Yield given. Multistep reaction;
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Dostert; Imbert; Langlois; et al.
European Journal of Medicinal Chemistry, 1984 , vol. 19, # 2 p. 105 - 110 Title/Abstract Full Text View citing articles Show Details
16
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Rx-ID: 5504172 Find similar reactions
Kashman,Y.; Cherkez,S.
Tetrahedron, 1972 , vol. 28, p. 155 - 165 Full Text View citing articles Show Details
Davies,W.A.M. et al.
Journal of the Chemical Society, 1960 , p. 3504 - 3512 Full Text View citing articles Show Details
Glushkov,R.G. et al.
Pharmaceutical Chemistry Journal, 1975 , vol. 9, # 12 p. 753 - 756 Khimiko-Farmatsevticheskii Zhurnal, 1975 , vol. 9, # 12 p. 6 - 9 Full Text View citing articles Show Details
O'Donovan; Keogh
Journal of the Chemical Society [Section] C: Organic, 1969 , p. 223,226 Full Text Show Details
Beyerman et al.
Recueil des Travaux Chimiques des Pays-Bas, 1963 , vol. 82, p. 1199,1220 Full Text Show Details
Singh; Razdan
Indian Journal of Chemistry, 1968 , vol. 6, p. 568 Full Text Show Details
Sato et al.
Bulletin of the Chemical Society of Japan, 1971 , vol. 44, p. 1708 Full Text Show Details
Montzka et al.
Tetrahedron Letters, 1974 , p. 1325 Full Text View citing articles Show Details
Schmidt et al.
Journal of Pharmaceutical Sciences, 1967 , vol. 56, p. 1453,1454 Full Text Show Details
Horak
Collection of Czechoslovak Chemical Communications, 1963 , vol. 28, p. 1614,1616 Full Text Show Details
Turner; Gearien
Journal of Pharmaceutical Sciences, 1964 , vol. 53, p. 1309,1312 Full Text Show Details
Niemer; Bucherer
Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1961 , vol. 326, p. 9,11 Full Text Show Details
Sekera
Annales de Chimie (Cachan, France), 1962 , vol. 7, # 13 p. 537,552,553 Full Text Show Details
Bottini; Gal
Journal of Organic Chemistry, 1971 , vol. 36, p. 1718 Full Text View citing articles Show Details
Polievktov et al.
Pharmaceutical Chemistry Journal, 1975 , vol. 9, # 6 p. 413,414,416,417 Khimiko-Farmatsevticheskii Zhurnal, 1975 , vol. 9, # 6 p. 56 Full Text View citing articles Show Details
17
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Rx-ID: 5504173 Find similar reactions
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Willstaetter; Bommer
Justus Liebigs Annalen der Chemie, 1921 , vol. 422, p. 30 Full Text View citing articles Show Details
Willstaetter
Patent: DE302401 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 1300 Full Text Show Details
18
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Rx-ID: 5504174 Find similar reactions
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Robinson
Journal of the Chemical Society, 1917 , vol. 111, p. 766 Full Text View citing articles Show Details
Erhitzen der sauren Loesung des Reaktionsprodukts;
19
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Rx-ID: 5504175 Find similar reactions
Merck
Patent: DE117630 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1145 Full Text Show Details
20
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Rx-ID: 5504176 Find similar reactions
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Willstaetter
Chemische Berichte, 1896 , vol. 29, p. 942 Chemische Berichte, 1901 , vol. 34, p. 142 Full Text View citing articles Show Details
Willstaetter
Patent: DE89597 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 1213 Full Text Show Details
Willstaetter
Chemische Berichte, 1896 , vol. 29, p. 398 Full Text View citing articles Show Details
T=60 - 70°C;
21
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Rx-ID: 5504177 Find similar reactions
Ciamician; Silber
Chemische Berichte, 1896 , vol. 29, p. 490 Gazzetta Chimica Italiana, 1896 , vol. 26 II, p. 161 Full Text View citing articles Show Details
22
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Rx-ID: 5504178 Find similar reactions
Willstaetter; Bode
Chemische Berichte, 1900 , vol. 33, p. 414 Full Text View citing articles Show Details
Willstaetter; Mueller,W.
Chemische Berichte, 1898 , vol. 31, p. 2660 Full Text View citing articles Show Details
23
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Rx-ID: 5504179 Find similar reactions
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Merck
Patent: DE117629 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1145 Full Text Show Details
T=60 - 70°C;
24
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Rx-ID: 5504180 Find similar reactions
With methanol
anschliessenden Hydrieren des Reaktionsgemisches an Raney-Nickel;
Lindenmann
Helvetica Chimica Acta, 1959 , vol. 42, p. 490,494 Full Text View citing articles Show Details
25
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Rx-ID: 5504181 Find similar reactions
Merck
Patent: DE117628 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1144 Full Text Show Details
Willstaetter
Chemische Berichte, 1900 , vol. 33, p. 1163 Justus Liebigs Annalen der Chemie, 1903 , vol. 326, p. 101 Full Text View citing articles Show Details
26
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Rx-ID: 5504182 Find similar reactions
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Merck
Patent: DE117628 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1144 Full Text Show Details
T=10°C;
27
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Rx-ID: 5504183 Find similar reactions
Merck
Patent: DE117629 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1145 Full Text Show Details
28
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Rx-ID: 5504184 Find similar reactions
Merck
Patent: DE344031 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 850 Full Text Show Details
Willstaetter
Patent: DE302401 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 849 Full Text Show Details
Willstaetter; Bommer
Justus Liebigs Annalen der Chemie, 1921 , vol. 422, p. 30
Full Text View citing articles Show Details
29
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Rx-ID: 5504185 Find similar reactions
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Willstaetter; Mueller
Chemische Berichte, 1898 , vol. 31, p. 1208 Full Text View citing articles Show Details
30
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Rx-ID: 5811655 Find similar reactions
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Robinson
Journal of the Chemical Society, 1917 , vol. 111, p. 766 Full Text View citing articles Show Details
31
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Rx-ID: 9060472 Find similar reactions
72%
With potassium carbonate in methanol
T=25°C; 2 h;
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Nicolaou; Montagnon; Baran; Zhong
Journal of the American Chemical Society, 2002 , vol. 124, # 10 p. 2245 - 2258 Title/Abstract Full Text View citing articles Show Details
32
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Rx-ID: 14732056 Find similar reactions
Multi-step reaction with 2 steps 1: 74 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 12 h / 75 °C 2: 72 percent / K2CO3 / methanol / 2 h / 25 °C View Scheme
Nicolaou; Montagnon; Baran; Zhong
Journal of the American Chemical Society, 2002 , vol. 124, # 10 p. 2245 - 2258 Title/Abstract Full Text View citing articles Show Details
33
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Rx-ID: 14732898 Find similar reactions
Multi-step reaction with 4 steps 1: 98 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 25 °C 2: 88 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 6 h / 65 °C 3: 74 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 12 h / 75 °C 4: 72 percent / K2CO3 / methanol / 2 h / 25 °C View Scheme
Nicolaou; Montagnon; Baran; Zhong
Journal of the American Chemical Society, 2002 , vol. 124, # 10 p. 2245 - 2258 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: 98 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 25 °C 2: 81 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 15 h / 80 °C 3: 72 percent / K2CO3 / methanol / 2 h / 25 °C View Scheme
Nicolaou; Montagnon; Baran; Zhong
Journal of the American Chemical Society, 2002 , vol. 124, # 10 p. 2245 - 2258 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: 76 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 22 h / 80 °C 2: 72 percent / K2CO3 / methanol / 2 h / 25 °C View Scheme
Nicolaou; Montagnon; Baran; Zhong
Journal of the American Chemical Society, 2002 , vol. 124, # 10 p. 2245 - 2258 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: 82 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 6 h / 65 °C 2: 74 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 12 h / 75 °C 3: 72 percent / K2CO3 / methanol / 2 h / 25 °C View Scheme
Nicolaou; Montagnon; Baran; Zhong
Journal of the American Chemical Society, 2002 , vol. 124, # 10 p. 2245 - 2258 Title/Abstract Full Text View citing articles Show Details
34
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Rx-ID: 14771020 Find similar reactions
Multi-step reaction with 3 steps 1: 88 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 6 h / 65 °C 2: 74 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 12 h / 75 °C 3: 72 percent / K2CO3 / methanol / 2 h / 25 °C View Scheme
Nicolaou; Montagnon; Baran; Zhong
Journal of the American Chemical Society, 2002 , vol. 124, # 10 p. 2245 - 2258 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: 81 percent / o-iodoxybenzoic acid / dimethylsulfoxide; fluorobenzene / 15 h / 80 °C 2: 72 percent / K2CO3 / methanol / 2 h / 25 °C View Scheme
Nicolaou; Montagnon; Baran; Zhong
Journal of the American Chemical Society, 2002 , vol. 124, # 10 p. 2245 - 2258 Title/Abstract Full Text View citing articles Show Details
35
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Rx-ID: 18795226 Find similar reactions
Multi-step reaction with 2 steps 1: 92 percent / Ag(I)F / acetonitrile / 0.33 h / Ambient temperature 2: 90 percent / Raney Nickel / ethyl acetate / 4 h / Ambient temperature View Scheme
Pandey; Lakshmaiah; Ghatak
Tetrahedron Letters, 1993 , vol. 34, # 45 p. 7301 - 7304 Title/Abstract Full Text View citing articles Show Details
36
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Multi-step reaction with 2 steps 1: PPh3*Br2 / acetonitrile; bis-(2-hydroxy-ethyl) ether / 2 h / 72 °C 2: K2CO3,H2/Ra Ni 28 / H2O / 0.5 h / 3.3 Torr
Rx-ID: 19039025 Find similar reactions
Sarel, Shalom; Dykman, Edmund
Heterocycles, 1981 , vol. 15, # 2 p. 719 - 734 Title/Abstract Full Text Show Details
View Scheme
Multi-step reaction with 2 steps 1: PPh3*Br2 / acetonitrile; bis-(2-hydroxy-ethyl) ether / 2 h / 72 °C 2: K2CO3,H2/Ra Ni 28 / H2O / 0.5 h / 3.3 Torr View Scheme
Sarel, Shalom; Dykman, Edmund
Heterocycles, 1981 , vol. 15, # 2 p. 719 - 734 Title/Abstract Full Text Show Details
37
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Rx-ID: 19202680 Find similar reactions
Multi-step reaction with 2 steps 1: CH2Cl2 / Ambient temperature 2: CH2Cl2 / Ambient temperature; also on treatment with dilute H2SO4
View Scheme
Moriarty, Robert M.; Prakash, Om; Vavilikolanu, Pushra R.
Synthetic Communications, 1986 , vol. 16, # 10 p. 1247 - 1254 Title/Abstract Full Text Show Details
38
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Rx-ID: 21879314 Find similar reactions
Multi-step reaction with 2 steps 1: ozonolysis 2: methanol; H2O View Scheme
Lansbury, Peter T.; Spagnuolo, Ciro J.; Grimm, Erich L.
Tetrahedron Letters, 1990 , vol. 31, # 28 p. 3965 - 3968 Title/Abstract Full Text View citing articles Show Details
39
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Rx-ID: 22183201 Find similar reactions
Karrer; Alagil
Helvetica Chimica Acta, 1947 , vol. 30, p. 1777 Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: ethanol / 100 °C 2: p-cymene; sodium / 160 °C View Scheme
40
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Rx-ID: 29676717 Find similar reactions
With 6 sodium amalgam; sodium dihydrogen phosphate monohydrate in methanol
T=20°C; 2 h;
Laha, Joydev K.
Chemistry of Natural Compounds, 2010 , vol. 46, # 2 p. 254 - 256 Title/Abstract Full Text View citing articles Show Details
41
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Rx-ID: 29725675 Find similar reactions
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Sienkiewicz, Michal; Lazny, Ryszard
Journal of Combinatorial Chemistry, 2010 , vol. 12, # 1 p. 5 - 8 Title/Abstract Full Text View citing articles Show Details
Stage #1: nortropinone Stage #2: methyl iodide in dichloromethane
Stage #3: With sodium acetate; acetic acid
T=100°C;
42
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Rx-ID: 37191198 Find similar reactions
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70%
Stage #1: 2,5-dimethoxy-tetrahydrofuran With hydrogenchloride in water
T=70°C; 0.5 h; Stage #2: acetone-1,3-dicarboxylic acid; N-methylamine hydrochloride T=40°C; pH=5.1; 1 h; Cooling with ice; Stage #3: With sodium chloride; sodium hydroxide
T=20°C; 1 h; Cooling with ice; Hide Experimental Procedure
Chiou, Wen-Hua; Chiang, Yu-Min; Chen, Guei-Tang
Tetrahedron Asymmetry, 2014 , vol. 25, # 1 p. 92 - 97 Title/Abstract Full Text View citing articles Show Details
Tropinone 2
A mixture of a solution of 2,5-dimethoxytetrahydrofuran (30.0mL, 231mmol, 1.0equiv), concentrated HCl (12M, 3.0mL), and water (70mL) was stirred at 70°C for 30min. Another acetate buffer solution was prepared as followed: to a 1-L flask charged with NaOH (36.2g, 905mmol, 3.9equiv) in an ice bath, was added water (170mL), followed by AcOH (51.8mL, 906mmol, 3.9equiv), acetonedicarboxylic acid (37.3g, 255mmol, 1.1equiv), methylamine hydrochloride salt (17.2g, 255mmol, 1.1equiv). To the buffer solution in an ice bath, was added slowly the acidic solution. The pH value of the combined solution was kept at 5.1. After stirring at 40°C for 1h, the cooled reaction mixture was added to an NaOH solution (50percent, 18.0mL) and NaCl (60.0g) in an ice bath. The mixture was stirred at room temperature for 1h, and then extracted with CH2Cl2 (150mL). The aqueous layer was then extracted with CH2Cl2 (100mL, five times). The combined organic layer was dried over anhydrous Na2SO4, and then concentrated under reduced pressure to give a crude brown product. The crude oil was purified by vaccum distillation, to afford a colorless oil (bp 60–65°C, 0.8mmHg). While standing at room temperature under normal pressure, the colorless liquid became a white solid (22.7g, 163mmol, 70percent): mp 41–42°C, [lit.: 40–42°C];12 Rf=0.19, EtOAc/n-hexane=1:2; 1H NMR (400MHz, 25°C, CDCl3, δ): 1.27–1.33 (m, 2H, H-6 and H-7), 1.80–1.83 (m, 2H, H-6 and H-7), 1.88 (d, J=16.0Hz, 2H, H-2 and H-4), 2.20 (s, 3H, – NCH3), 2.39 (dd, J=4.8 and 16.0Hz, 2H, H-2 and H-4), 3.15 (br s, 2H, H-1 and H-5); 13C NMR (100MHz, 25°C, CDCl3, δ): 27.1 (t, 2C, C-6 and C-7), 37.7 (q, –NCH3), 46.9 (t, 2C, C-2 and C-4), 60.1 (d, 2C, C-1 and C-5), 208.7 (s, C-3); EI-HRMS (m/z): [M]+ calcd for C8H13NO+, 139.0997; found, 139.0990 (Δ=5.0ppm).
43
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Rx-ID: 38175157 Find similar reactions
250 g
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Stage #1: 2,5-dimethoxy-tetrahydrofuran With sodium hydrogencarbonate in water
T=85 - 90°C; 2 h; Stage #2: acetone-1,3-dicarboxylic acid; methylamine in water
T=-5 - 25°C; pH=7; Hide Experimental Procedure
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MYLAN LABORATORIES LTD.; GORE, Vinayak; JOSHI, Rajesh; TRIPATHI, Anil Kumar; JADHAV, Madhav; BHANDARI, Shreyas
Patent: WO2014/102829 A1, 2014 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details
1:Preparation of tropinone
In a round bottom flask charge water 1000 ml, 500 gm of 2, 5-dimethoxy tetrahydrofuran (3.783 mol) and 10 ml cone. The reaction mixture was heated to 85-90°C for 2 hrs. After 2 hours the reaction mixture was allowed to cool to 25-30°C and further chilled the reaction mass to -5 to-10°C. In the above reaction mass 553 g of 1, 3 acetone dicarboxylic acid (3.783 mol) was added under stirring at -5 to 0°C and 1000 ml water was added and chilled to -5 to 0°C. In the reaction mass 440 g of aq. mono methyl amine (40percent solution) (5.67 mol) as added drop wise at temp. -5 to 0°C (Caution: Exotherm was observed during addition of monomethyl amine). Raise the temp, of reaction mixture to 5 to 10 °C and added portion wise 54.2 g of sodium bicarbonate to get pH 7 to 8. After the addition of sodium bicarbonate is completed, flushed the reaction mass with 500 ml of water. The temperature of the reaction mixture was raised to 20-25 °C. The progress of reaction was monitored by GC (unreacted 2,5-dimethoxy tetrahydrofuran is <5percent). After completion of reaction extracted the reaction mass with 6x 2.5 litre dichloromethane. The combine dichloromethane layer and distilled the solvent at bath temp. 50-55°C to get crude tropinone. The crude tropinone was distilled under vacuum (-15 mbar) and oil temp. 125-130°C and vapour temp. 105-110°C to get 250 g of pure tropinone (GC purity >95percent). Yield = 250 g (0.5 w/w) Theoretical yield = (1.05 w/w) Molar yield = 47.6 percent
44
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Rx-ID: 40187596 Find similar reactions
84%
With Ag/TiO2
T=25°C; P=760.051 Torr; 10 h; UV-irradiation;
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Tsarev, Vasily N.; Morioka, Yuna; Caner, Joaquim; Wang, Qing; Ushimaru, Richiro; Kudo, Akihiko; Naka, Hiroshi; Saito, Susumu
Organic Letters, 2015 , vol. 17, # 10 p. 2530 - 2533 Title/Abstract Full Text View citing articles Show Details
45
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Rx-ID: 42574503 Find similar reactions
With pyridinium chlorochromate in dichloromethane
T=20°C;
Yin, Xiu-Juan; Geng, Chang-An; Huang, Xiao-Yan; Chen, Hao; Ma, Yun-Bao; Chen, Xing-Long; Sun, Chang-Li; Yang, Tong-Hua; Zhou, Jun; Zhang, Xue-Mei; Chen, JiJun
RSC Advances, 2016 , vol. 6, # 51 p. 45059 - 45063 Title/Abstract Full Text View citing articles Show Details
46
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Rx-ID: 1805887 Find similar reactions
Majewski, Marek; Zheng, Guo-Zhu
Canadian Journal of Chemistry, 1992 , vol. 70, # 10 p. 2618 - 2626 Title/Abstract Full Text Show Details
Yield given. Multistep reaction;
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Rx-ID: 29125576 Find similar reactions
62%
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Stage #1: [2-(2)H]2,5-dibutoxytetrahydrofuran With hydrogenchloride in water
T=100°C; 2 h; Stage #2: acetone-1,3-dicarboxylic acid; methylamine With hydrogenchloride; sodium acetate in water
T=50°C; Robinson reaction; 2 h;
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Fournial, Anais; Ranaivondrambola, Tsiresy; Mathe-Allainmat, Monique; Robins, Richard J.; Lebreton, Jacques
European Journal of Organic Chemistry, 2010 , # 1 p. 152 - 156 Title/Abstract Full Text View citing articles Show Details
48
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Rx-ID: 3229885 Find similar reactions
Majewski, Marek; Zheng, Guo-Zhu
Canadian Journal of Chemistry, 1992 , vol. 70, # 10 p. 2618 - 2626 Title/Abstract Full Text Show Details
Yield given. Multistep reaction;
49
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Rx-ID: 6588952 Find similar reactions
Blossey et al.
Tetrahedron, 1964 , vol. 20, p. 585,595 Full Text Show Details
6,7-d2-Tropin/Acn., Chrom(VI)oxyd, 0grad;
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Rx-ID: 19589629 Find similar reactions
Majewski, Marek; Zheng, Guo-Zhu
Canadian Journal of Chemistry, 1992 , vol. 70, # 10 p. 2618 - 2626 Title/Abstract Full Text Show Details
51
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Rx-ID: 29125578 Find similar reactions
Stage #1: [2,5-(2)H2]2,5-dibutoxytetrahydrofuran With hydrogenchloride; water T=100°C; 2 h; Stage #2: acetone-1,3-dicarboxylic acid; methylamine With hydrogenchloride; sodium acetate in water
T=10 - 50°C; Robinson reaction; 2 h;
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Fournial, Anais; Ranaivondrambola, Tsiresy; Mathe-Allainmat, Monique; Robins, Richard J.; Lebreton, Jacques
European Journal of Organic Chemistry, 2010 , # 1 p. 152 - 156 Title/Abstract Full Text View citing articles Show Details
52
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Rx-ID: 6588382 Find similar reactions
aus kaeufl. 3-14C-Citronensaeure nach Robinson;
Eling et al.
Journal of Pharmaceutical Sciences, 1968 , vol. 57, p. 1357,1359 Full Text Show Details
(yield)65-67percent markierte Verb.;
Eling et al.
Journal of Pharmaceutical Sciences, 1968 , vol. 57, p. 1357,1359 Full Text Show Details
53
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Rx-ID: 6653258 Find similar reactions
Schmidt; Eling; McOwen
Journal of pharmaceutical sciences, 1968 , vol. 57, # 3 p. 443 - 446 Title/Abstract Full Text View citing articles Show Details
Acetondicarbonsaeurediethylester, Succindialdehyd, (14C)H3-NH2*HCl;
Basey; Woolley
Phytochemistry (Elsevier), 1975 , vol. 14, p. 2201,2203 Full Text Show Details
Methylamin-<14C>-hydrochlorid, Acetondicarbonsaeure, Bernsteinsaeuredialdehyd <W., pH:5.4; N2 im Vakuum; 24h, 20-22grad>;
Werner et al.
Justus Liebigs Annalen der Chemie, 1961 , vol. 644, p. 109,115 Full Text Show Details
(yield)70percent;
Werner et al.
Justus Liebigs Annalen der Chemie, 1961 , vol. 644, p. 109,115 Full Text Show Details
54
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Rx-ID: 1514794 Find similar reactions
25%
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With hydrogenchloride; disodium hydrogenphosphate; sodium dihydrogenphosphate in water
1.) room temperature, 3 d, 2.) reflux, 10 min;
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Robins, Richard J.; Bachmann, Peter; Woolley, Jack G.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994 , # 6 p. 615 - 620 Title/Abstract Full Text View citing articles Show Details
55
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Rx-ID: 349068 Find similar reactions
Closs
Journal of the American Chemical Society, 1959 , vol. 81, p. 5456,5459 Full Text View citing articles Show Details
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Rx-ID: 5442694 Find similar reactions
Blossey et al.
Tetrahedron, 1964 , vol. 20, p. 585,595 Full Text Show Details
Tropinon, Natrium/Deuteriumoxyd, Siedetemp.;
A
B
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57
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A: 50% B: 37%
Moriarty, Robert M.; Prakash, Om; Vavilikolanu, Pushpa R.; Vaid, Radhe K.; Freeman, Wade A.
Journal of Organic Chemistry, 1989 , vol. 54, # 16 p. 4008 - 4010 Title/Abstract Full Text View citing articles Show Details
With iodosylbenzene; boron trifluoride diethyl etherate in water
T=0 - 10°C; 4 h;
A
B
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58
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A: 55% B: 13%
With phosphate buffer in water
T=20°C; Decarboxylation; demethoxycarbonylation; pH=8.0; 24 h;
Node, Manabu; Nakamura, Soichi; Nakamura, Daisaku; Katoh, Takahiro; Nishide, Kiyoharu
Tetrahedron Letters, 1999 , vol. 40, # 29 p. 5357 - 5360 Title/Abstract Full Text View citing articles Show Details
A
B
59
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Rx-ID: 144051 Find similar reactions
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With disodium hydrogenphosphate; water
bei pH 6.8;
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Findlay
Journal of Organic Chemistry, 1957 , vol. 22, p. 1385,1388, 1392 Journal of Organic Chemistry, 1958 , vol. 23, p. 391,393 Full Text View citing articles Show Details
A
B
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60
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Rx-ID: 6684481 Find similar reactions
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Findlay
Journal of Organic Chemistry, 1957 , vol. 22, p. 1385,1388, 1392 Journal of Organic Chemistry, 1958 , vol. 23, p. 391,393 Full Text View citing articles Show Details
pH 6.8;
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Rx-ID: 40386764 Find similar reactions
in toluene
T=20°C;
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Sidorowicz, Katarzyna; Lazny, Ryszard; Nodzewska, Aneta; Wolosewicz, Karol; Ratkiewicz, Artur; Urbanczyk-Lipkowska, Zofia; Kalicki, Przemyslaw
Tetrahedron, 2015 , vol. 71, # 32 art. no. 26735, p. 5148 - 5158 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
E
F
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in water
720 h; Irradiationdecomposition in aq. solution; stability after storage in glass and polyethylene containers under various conditions (pH-value, temp., oxidative effects, irradiation);
Jira; Pohloudek-Fabini
Die Pharmazie, 1982 , vol. 37, # 9 p. 645 - 649 Title/Abstract Full Text View citing articles Show Details