Water → 3-[(4-Chlorophenyl)methyl]-6,6-dimethylcyclohex-2-en-1-one

HRID 1886563Notes

Reaction equation

HRID 1886563 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2(O)[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:19].[Na+].[Na+].S(=O)(=O)(O)O.O>C(OCC)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9](=[O:19])[CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 25408Sodium DichromateHCID 19771306HCID 19771306, compound2×

Product 1

HCID 197713053-[(4-Chlorophenyl)methyl]-6,6-dimethylcyclohex-2-en-1-oneYield 189.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of the 1-(4-chlorobenzyl)-4,4-dimethylcyclohex-2-en-1-ol (368 g, 1.47 mol) obtained in (a) in 40/60 petroleum (40 ml) was added in a steady stream to a solution of sodium dichromate (217 g, 0.74 mol) in dilute sulphuric acid (250 g, 2.6 mol 98% sulphuric acid in 1.5 liters of water). The reaction mixture was then held at a temperature between 10° and 30° C. and stirred for 40 minutes. Water (500 ml) and diethyl ether (700 ml) were added and the aqueous layer extracted twice with diethyl ether (2×700 ml). The organic phases were then combined and backwashed with saturated sodium bicarbonate solution (1×500 ml) and water (1×500 ml). The solvent was then flashed off to give 349 g crude 1-(4-chlorobenzyl)-4,4-dimethylcyclohex-1-en-3-one as a beige coloured granular solid. Trituration in petrol gave a pure sample of the desired product, m.pt. 87°-90° C.

Workup

  1. customwas then held at a temperature between 10° and 30° C.
  2. extractionthe aqueous layer extracted twice with diethyl ether (2×700 ml)

Sources & evidence

ORD record
ord-cca6e29dfbe54ae1b821e0c54d55f079
Source dataset
uspto-grants-1992_09
Patent number
US05151550

Reaction notes

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