Methyl 4-acetylbenzoate → Methyl 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoate

HRID 1821155Notes

Reaction equation

HRID 1821155 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:14]([Si](C)(C)C)([F:17])([F:16])[F:15].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOCC>[F:15][C:14]([F:17])([F:16])[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)([OH:3])[CH3:2]

Participants

6

Reactant 3

HCID 137990Methyl 4-acetylbenzoateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 57892524Methyl 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoateYield 86%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-acetylbenzoate (5.0 g, 28.1 mmol) and CF3SiMe3 (12.5 mL, 84.2 mmol) in THF (150 mL) was added TBAF (1.0 M, 78.6 mL, 78.6 mmol) dropwise at 0° C. The mixture was stirred for 2.5 h at room temperature, diluted with Et2O (100 mL). The solution was washed with saturated aqueous NaHCO3 and brine, dried and concentrated. Flash chromatography of the residue, using 2:8 EtOAc-Hexane, gave methyl 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoate (6.0 g). 1H NMR (CDCl3) δ 8.07(d, J=8.5 Hz, 2 H), δ 7.67(d, J=8.5 Hz, 2 H), 3.93(s, 3 H), 2.70(br, 1 H), 1.80(s, 3H). MS 249.1 (M+H+).

Workup

  1. washThe solution was washed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eed2c923183d4294a7f1b922cc912cf8
Source dataset
uspto-grants-2009_10
Patent number
US07605289B2

Reaction notes

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