Benzaldehyde → 2-Methyl-6-(phenylmethylene)cyclohexanone

HRID 1599791Notes

Reaction equation

HRID 1599791 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>O>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4](=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]1=[O:8]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 114192-MethylcyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 977022-Methyl-6-(phenylmethylene)cyclohexanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

It is also known to react 2-methylcyclohexanone with benzaldehyde in the presence of a solution of sodium hydroxide in a mixture of 37.5% by volume alcohol and 62% by volume water. In this way, it is possible over the course of 3 hours to obtain, in a yield of from 65 to 70%, 2-benzal-6-methylcyclohexanone (=2-methyl-6-benzylidenecyclohexanone (see J. Am. Chem. Soc. 65, 1317 (1943)). Disadvantages are the relatively low yield and the fact that the product is obtained as an oil which must be extracted and worked up by distillation.

Workup

  1. customis possible over the course of 3 hours

Sources & evidence

ORD record
ord-5f51f7df3b3c408ba050f7be5a29904c
Source dataset
uspto-grants-1998_04
Patent number
US05741937

Reaction notes

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