3,4,5-Trifluorobenzaldehyde → 3,4,5-Trifluorobenzyl alcohol

HRID 240970Notes

Reaction equation

HRID 240970 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[F:10])[CH:5]=[O:6].O.[BH4-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([F:11])[C:9]=1[F:10]

Participants

4

Reactant 2

HCID 27769543,4,5-TrifluorobenzaldehydeHCID 131728255water NaBH4

Product 1

HCID 27770403,4,5-Trifluorobenzyl alcoholYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−5° C.) solution of 3,4,5-trifluorobenzaldehyde (7.0 g, 43.75 mmol) in a mixture (50 ml, 9:1) of THF and water NaBH4 (1.662 g, 43.75 mmol) was slowly added in portions over a period of 30 min. The reaction mixture was allowed to attain room temperature over a period of 2 h and carefully poured into ice-cold dil HCl (200 ml, IN). The oily layer was extracted into CH2Cl2 (250 ml) and the organic layer washed with water (200 ml), dried (MgSO4) and evaporated. The crude product (7.08 g, quantitative) obtained was taken forward without further purification.

Workup

  1. additionwas slowly added in portions over a period of 30 min
  2. extractionThe oily layer was extracted into CH2Cl2 (250 ml)
  3. washthe organic layer washed with water (200 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7beca9cb5c5a495dac86143137bef941
Source dataset
uspto-grants-2014_02
Patent number
US08648116B2

Reaction notes

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