4-Methylbenzaldehyde → 4-Methyl-alpha-(trifluoromethyl)benzenemethanol

HRID 1186352Notes

Reaction equation

HRID 1186352 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[F:10][C:11]([Si](C)(C)C)([F:13])[F:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:10][C:11]([F:13])([F:12])[CH:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1)[OH:8]

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 3472044-Methyl-alpha-(trifluoromethyl)benzenemethanolYield 125.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of p-tolualdehyde (500 μL, 4.24 mmol), (trifluoromethyl)trimethylsilane (752 μL, 5.09 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 424 μL, 0.424 mmol) and tetrahydrofuran (10 mL), the mixture was stirred and reacted at room temperature for 30 minutes. Thus, 4-(2,2,2-trifluoro-1-hydroxyethyl)toluene (Compound DE) (1.01 g, yield: quantitative) was obtained.

Workup

  1. customreacted at room temperature for 30 minutes

Sources & evidence

ORD record
ord-8118ef3b9ab54d32afe11971fb347ed7
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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