Water → 3,4-Dimethyl-cyclohex-3-enecarboxylic acid
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
Product 1
Reagents, catalysts & solvents 1
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
Reaction notes
Loading…