Acetone → 4-Chloro-alpha,alpha-dimethylphenethylic alcohol

HRID 1732486Notes

Reaction equation

HRID 1732486 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[Mg].[CH3:11][C:12]([CH3:14])=[O:13].Cl>CCOCC>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:12]([CH3:14])([OH:13])[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 5462224Magnesium

Product 1

HCID 796094-Chloro-alpha,alpha-dimethylphenethylic alcoholYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-chlorobenzyl chloride (165 g; 1.02 mole) in ether (500 ml) was added dropwise during one hour to magnesium (24.3 g; 1.00 mole) in a three-necked flask equipped with stirrer and reflux condenser. The spontaneous reflux was allowed to continue for another hour and the solution was cooled. Acetone (60.0 g, 1.30 mole) was added dropwise and the solution heated to reflux for three hours. After cooling, the reaction mixture was poured out on ice (500 ml) and concentrated hydrochloric acid (92 ml). The phases were separated. The organic phase was washed with water, dried (Na2SO4) and evaporated in vacuum. The residual oil was fractionated affording 1-(4-chlorophenyl)-2-methyl-2-propanol (b.p. 123°-124° C./12 mm Hg; nD25 =1.5300; 128.5 g, 70% yield).

Workup

  1. customequipped with stirrer
  2. temperaturereflux condenser
  3. temperatureThe spontaneous reflux
  4. waitto continue for another hour
  5. temperaturethe solution was cooled
  6. temperaturethe solution heated
  7. temperatureto reflux for three hours
  8. temperatureAfter cooling
  9. customThe phases were separated
  10. washThe organic phase was washed with water
  11. dry with materialdried (Na2SO4)
  12. customevaporated in vacuum

Sources & evidence

ORD record
ord-eb7785c97a3e41288104d1c2d3d0c8e2
Source dataset
uspto-grants-1980_12
Patent number
US04237311

Reaction notes

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