1-Chloro-4-(chloromethyl)benzene → 1-[(4-Chlorophenyl)methyl]-4,4,6-trimethylcyclohex-2-en-1-ol

HRID 1886565

Reaction equation

HRID 1886565 reaction equation
[Mg].[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[CH3:11][C:12]1([CH3:20])[CH2:17][CH:16]([CH3:18])[C:15](=[O:19])[CH:14]=[CH:13]1.[Cl-].[NH4+]>C(OCC)C>[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][C:15]2([OH:19])[CH:16]([CH3:18])[CH2:17][C:12]([CH3:20])([CH3:11])[CH:13]=[CH:14]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 25517Ammonium ChlorideHCID 1145072-Cyclohexen-1-one, 4,4,6-trimethyl-HCID 5462224Magnesium

Product 1

HCID 197713021-[(4-Chlorophenyl)methyl]-4,4,6-trimethylcyclohex-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a slurry of magnesium turnings (66 g, 2.73 g atoms) in diethyl ether (300 ml) was added a solution of 4-chlorobenzyl chloride (418 g, 2.6 moles) in diethyl ether (1500 ml) at such a rate as to maintain gentle reflux. After a further 30 minutes, a solution of 4,4,6-trimethylcyclohex-2-en-1-one (340 g, 2.46 moles) in diethyl ether (350 ml) was added, again maintaining a gentle reflux. After 1 hour the mixture was added into saturated aqueous ammonium chloride (4 liters) and the phases separated. The ether phase was back-washed with water (1 liter) and used directly in the next reaction. A small portion of 1-(4-chlorobenzyl)-4,4,6-trimethylcyclohex-2-en-1-ol was isolated for characterisation (gas chromatography analysis showed two isomers in approximately equal amounts).

Workup

  1. temperatureto maintain gentle reflux
  2. temperatureagain maintaining a gentle reflux
  3. customthe phases separated
  4. washThe ether phase was back-washed with water (1 liter)
  5. customused directly in the next reaction

Sources & evidence

ORD record
ord-09fcd51e7a864ab9b60bd36e94d954ac
Source dataset
uspto-grants-1992_09
Patent number
US05151550

Linked notes

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