Methyl Acrylate → 3-Cyclohexene-1-carboxylic acid, 3,4-dimethyl-, methyl ester

HRID 625164Notes

Reaction equation

HRID 625164 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH3:7][C:8]([C:10]([CH3:12])=[CH2:11])=[CH2:9]>C1(C)C=CC=CC=1>[CH3:9][C:8]1[CH2:7][CH:2]([C:1]([O:5][CH3:6])=[O:4])[CH2:3][CH2:11][C:10]=1[CH3:12]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 105662,3-Dimethyl-1,3-butadiene

Product 1

HCID 5726673-Cyclohexene-1-carboxylic acid, 3,4-dimethyl-, methyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl acrylate (1 eq.) and 2,3-dimethylbuta-1,3-diene (1.1 eq.) in toluene (2M) was pumped through a heated coil reactor at 220° C. with a residence time of 17 minutes. The resulting mixture was concentrated under reduced pressure and yielded the product as colorless oil (87% yield).

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a794476bcefe477eb7ca51f1272dffef
Source dataset
uspto-grants-2016_04
Patent number
US09303232B2

Reaction notes

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