Benzoic acid, 4-methoxy-, (1S,2S,4R)-4-methyl-5-methylene-3-oxobicyclo[2.2.2]oct-2-yl ester

Base Information

Chemical Name:Benzoic acid, 4-methoxy-, (1S,2S,4R)-4-methyl-5-methylene-3-oxobicyclo[2.2.2]oct-2-yl ester
CAS No.:685108-90-1
Molecular Formula:C₁₈H₂₀O₄
Molecular Weight:300.354
Hs Code.:

Synonyms:

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Chemical Property of Benzoic acid, 4-methoxy-, (1S,2S,4R)-4-methyl-5-methylene-3-oxobicyclo[2.2.2]oct-2-yl ester

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Technology Process of Benzoic acid, 4-methoxy-, (1S,2S,4R)-4-methyl-5-methylene-3-oxobicyclo[2.2.2]oct-2-yl ester

There total 6 articles about Benzoic acid, 4-methoxy-, (1S,2S,4R)-4-methyl-5-methylene-3-oxobicyclo[2.2.2]oct-2-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 210633-85-5
(3aS,4R,7S,7aR)-3a,4,7,7a-tetrahydro-2,2,7-trimethyl-4,7-ethano-1,3-benzodioxol-8-one

: 685108-90-1
(1R,3S,4S)-1-methyl-6-methylene-2-oxobicyclo[2.2.2]octan-3-yl 4-methoxybenzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / hydrogen / palladium on carbon / ethanol / 16 h / 18 °C / 760 Torr

2.1: 86 percent / acetic acid / H₂O / 18 h / 80 °C

3.1: 100 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran / 2 h / 0 °C

4.1: 89 percent / dimethylsulfoxide / 1 h / 18 °C

5.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 4 h / 18 °C

5.2: 175 mg / trifluoroacetic anhydride; dimethylsulfoxide / CH₂Cl₂ / 3 h / -60 °C

With hydrogen; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; 4.1: Wittig reaction / 5.2: Swern oxidation;
DOI:10.1071/CH03164

Reference yield:

: (3aS,4R,7S,7aR)-8-chloro-3a,4,7,7a-tetrahydro-2,2,7-trimethyl-4,7-ethano-1,3-benzodioxole-8-carbonitrile

: 685108-90-1
(1R,3S,4S)-1-methyl-6-methylene-2-oxobicyclo[2.2.2]octan-3-yl 4-methoxybenzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 81 percent / potassium hydroxide / H₂O / 16 h / Heating

2.1: 96 percent / hydrogen / palladium on carbon / ethanol / 16 h / 18 °C / 760 Torr

3.1: 86 percent / acetic acid / H₂O / 18 h / 80 °C

4.1: 100 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran / 2 h / 0 °C

5.1: 89 percent / dimethylsulfoxide / 1 h / 18 °C

6.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 4 h / 18 °C

6.2: 175 mg / trifluoroacetic anhydride; dimethylsulfoxide / CH₂Cl₂ / 3 h / -60 °C

With potassium hydroxide; hydrogen; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; 5.1: Wittig reaction / 6.2: Swern oxidation;
DOI:10.1071/CH03164

Reference yield:

: 685108-86-5
(2S,3aR,4R,7S,7aS)-hexahydro-2-(4-methoxyphenyl)-4-methyl-5-methylene-4,7-ethano-1,3-benzodioxole

: (1S,3R,4R)-4-methyl-5-methylene-2-oxobicyclo[2.2.2]octan-3-yl 4-methoxybenzoate

: 685108-90-1
(1R,3S,4S)-1-methyl-6-methylene-2-oxobicyclo[2.2.2]octan-3-yl 4-methoxybenzoate

Guidance literature:: (2S,3aR,4R,7S,7aS)-hexahydro-2-(4-methoxyphenyl)-4-methyl-5-methylene-4,7-ethano-1,3-benzodioxole; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 18 ℃; for 4h;

With dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; at -60 ℃; for 3h;
DOI:10.1071/CH03164