3,5-Bis(trifluoromethyl)benzaldehyde → 3,5-Bis(trifluoromethyl)benzyl alcohol

HRID 1358793Notes

Reaction equation

HRID 1358793 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=[O:7].[H][H]>[Ni].C1(C)C=CC=CC=1>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:10]=1)[CH2:6][OH:7]

Participants

5

Reactant 2

HCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 1229333,5-Bis(trifluoromethyl)benzyl alcoholYield 82.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1140TolueneSolvent

Procedure

37 g of 3,5-bis(trifluoromethyl)benzaldehyde and 4 g of Raney nickel together with 150 ml of toluene were placed in a reaction vessel at room temperature. The vessel was pressurized with 30 bar of hydrogen gas and the mixture was hydrogenated at 50° C. for 7.5 hours while stirring. The mixture was subsequently cooled to room temperature, depressurized and the catalyst was filtered off. The filtrate was evaporated and the crude product obtained in this way was distilled at 17 mbar. 3,5-bis(trifluoro-methyl)benzyl alcohol having a boiling point of 97° C. was obtained in a yield of 31.5 g and a purity of 97.7%. This corresponds to a yield of 82.5% of theory.

Workup

  1. filtrationthe catalyst was filtered off
  2. customThe filtrate was evaporated
  3. customthe crude product obtained in this way
  4. distillationwas distilled at 17 mbar

Sources & evidence

ORD record
ord-70cebbb2e6ef4da1ab77095b7f46c662
Source dataset
uspto-grants-2003_07
Patent number
US06596906B2

Reaction notes

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