4-Chlorobenzaldehyde → HCID 54289634, compound

HRID 846344Notes

Reaction equation

HRID 846344 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3]1.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[OH-].[Na+]>O>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[C:5]2[CH2:6][CH2:7][C:2]([CH3:9])([CH3:1])[CH2:3][C:4]2=[O:8])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 76322Cyclohexanone, 3,3-dimethyl-

Product 1

HCID 54289634HCID 54289634, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,3-dimethylcyclohexanone (34 g, 0.27 mole) and 4-chlorobenzaldehyde (38 g, 0.27 mole) in water (100 ml) containing sodium hydroxide (5.4 g, 0.27 mole) was refluxed for 24 hours. On cooling, the mixture was extracted with toluene and flashed to give 48g 2-(4-chlorobenzylidene)-5,5-dimethylcyclohexanone after crystallisation from methanol. M.pt. 85-6° C. Yield: 75%.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureOn cooling
  3. extractionthe mixture was extracted with toluene

Sources & evidence

ORD record
ord-7d4dc30dc3954db1852e0a7b69560d06
Source dataset
uspto-grants-1992_08
Patent number
US05136081

Reaction notes

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