Acetone → 2-(3,5-Bis(trifluoromethyl)phenyl)propan-2-ol

HRID 1860961Notes

Reaction equation

HRID 1860961 reaction equation
[Mg].[F:2][C:3]([F:16])([F:15])[C:4]1[CH:5]=[C:6](Br)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[CH3:17][C:18]([CH3:20])=[O:19].[Cl-].[NH4+]>C(OCC)C>[F:2][C:3]([F:16])([F:15])[C:4]1[CH:5]=[C:6]([C:18]([OH:19])([CH3:20])[CH3:17])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 676021-Bromo-3,5-bis(trifluoromethyl)benzeneHCID 5462224Magnesium

Product 1

HCID 6207792-(3,5-Bis(trifluoromethyl)phenyl)propan-2-olYield 99.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

16.10 g (0.659 mol) of magnesium turnings was treated under argon in 450 ml of diethyl ether with 150 g (0.507 mol) of 3,5-bis-trifluoromethylbromobenzene at 33° C. for 1.5 h. Then a solution of 56.0 ml (0.763 mol) of acetone in 100 ml of diethylether was added at 16-22° C. under stirring. 110 ml of 25% Ammonium chloride solution was added at ca. 20° C. after 1.5 h to the reaction mixture and the suspension stirred for 1 h. The organic phase was dried over sodium sulfate, rotary evaporated and finally dried at 35° C. and 10 mbar, affording 136.96 g of 2-(3,5-bis-trifluoromethyl-phenyl)-propan-2-ol, which had a 99.2% purity according to GC analysis. Light yellow crystals, m.p. 59-60° C.

Workup

  1. stirringthe suspension stirred for 1 h
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customrotary evaporated
  4. customfinally dried at 35° C.

Sources & evidence

ORD record
ord-c533809607444ad3bc1c62f7e12b396c
Source dataset
uspto-grants-2003_03
Patent number
US06531597B2

Reaction notes

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