Water → 3,4-Dimethyl-cyclohex-3-enecarboxylic acid

HRID 71049

Reaction equation

HRID 71049 reaction equation
[CH3:1][C:2]([C:4]([CH3:6])=[CH2:5])=[CH2:3].[C:7]([OH:11])(=[O:10])[CH:8]=[CH2:9].BrC1C=CC=CC=1B(O)O.O>C(Cl)Cl>[CH3:3][C:2]1[CH2:1][CH:8]([C:7]([OH:11])=[O:10])[CH2:9][CH2:5][C:4]=1[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6581Acrylic AcidHCID 105662,3-Dimethyl-1,3-butadieneHCID 2773294(2-Bromophenyl)boronic acid

Product 1

HCID 114578033,4-Dimethyl-cyclohex-3-enecarboxylic acidYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dimethylbuta-1,3-diene (2 equiv.) and acrylic acid (1 equiv.) were combined in the presence of 2-bromophenyl boronic acid (0.2 equiv.) and water (0.1 equiv.) in DCM at room temperature for 28 hours. The product, 3,4-dimethylcyclohex-3-enecarboxylic acid, was isolated in 76% yield. When the reaction was repeated without the addition of water, the yield was 90%.

Sources & evidence

ORD record
ord-83cc71921fff41288cdf45226d2ff84a
Source dataset
uspto-grants-2014_09
Patent number
US08822720B2

Linked notes

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