1-Phenyl-1-propanone → alpha-Ethyl-3-(trifluoromethyl)benzhydrol

HRID 839305Notes

Reaction equation

HRID 839305 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[Mg].[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[C:16](Br)[CH:17]=[CH:18][CH:19]=1.[Cl-].[NH4+]>CCOCC>[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[C:1]([CH2:2][CH3:3])([OH:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 71481-Phenyl-1-propanoneHCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 41870alpha-Ethyl-3-(trifluoromethyl)benzhydrol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 37.5 g. of propiophenone in 200 ml. of dry ether is added dropwise to a -10° C Grignard solution prepared from 13.6 g. of magnesium turnings and 126 g. of 3-trifluoromethyl-bromobenzene in 182 ml. of dry ether. The reaction mixture is stirred at 0° C for 30 minutes, thereafter refluxed for 1 hour. The mixture is cooled to 0° C, and the Grignard complex is decomposed with a 10% aqueous ammonium chloride solution. The ethereal phase is separated, washed until neutral, and dried over anhydrous sodium sulfate. The solvent is evaporated, and the residual oil is subjected to fractional distillation in vacuo. This way 57.3 g. of 3-trifluoromethyl-α-ethyl-benzhydrol are obtained: b.p.: 106°-108° C/0.03mmHg.

Workup

  1. customprepared from 13.6 g
  2. temperaturerefluxed for 1 hour
  3. temperatureThe mixture is cooled to 0° C
  4. customThe ethereal phase is separated
  5. washwashed until neutral, and
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent is evaporated
  8. distillationthe residual oil is subjected to fractional distillation in vacuo

Sources & evidence

ORD record
ord-fe3b5aa997bb4bd09c3beed9d10ebf43
Source dataset
uspto-grants-1978_06
Patent number
US04094908

Reaction notes

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