1-(3-Chlorophenyl)ethanone → Benzenemethanol, 3-chloro-.alpha.,.alpha.-dimethyl-

HRID 1364447Notes

Reaction equation

HRID 1364447 reaction equation
[CH3:1][Mg]Br.[CH3:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)=[O:6]>CCOCC>[Cl:13][C:9]1[CH:8]=[C:7]([C:5]([OH:6])([CH3:1])[CH3:4])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 149331-(3-Chlorophenyl)ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 593110Benzenemethanol, 3-chloro-.alpha.,.alpha.-dimethyl-Yield 93.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methylmagnesium bromide (3.6 mL, 10.67 mmol, Aldrich, 3 M solution in ether) was added to a cooled (−10° C.) solution of 3-chloroacetophenone (1.5 g, 9.7 mmol) in anhydrous ether slowly over 30 min. After complete addition, the reaction mixture was slowly warmed to room temperature, stirred for 18 hours. Again cooled (−5° C.), than quenched with sat. ammonium chloride solution over 30 min. The reaction mixture was extracted with ether, dried, filtered and concentrated to afford 1.55 g of 2-(3-chlorophenyl)propan-2-ol.

Workup

  1. additionAfter complete addition
  2. temperatureAgain cooled (−5° C.)
  3. customthan quenched with sat. ammonium chloride solution over 30 min
  4. extractionThe reaction mixture was extracted with ether
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-908307a7f4c64e7bb57029ee691457c9
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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