Sodium borohydride → 3-Methyl-2,4,5,6-tetrafluorobenzyl alcohol

HRID 1583464Notes

Reaction equation

HRID 1583464 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[C:5]([F:15])=[C:6]([C:9]([F:14])=[C:10]([F:13])[C:11]=1[F:12])[CH:7]=[O:8]>CO>[CH3:3][C:4]1[C:5]([F:15])=[C:6]([C:9]([F:14])=[C:10]([F:13])[C:11]=1[F:12])[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 130753183-Methyl-2,4,5,6-tetrafluorobenzaldehyde

Product 1

HCID 130753193-Methyl-2,4,5,6-tetrafluorobenzyl alcoholYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.3 g) was added in small portions to a solution of 3-methyl-2,4,5,6-tetrafluorobenzaldehyde (1.5 g) in methyl alcohol (15 ml) at the ambient temperature, after which the mixture was heated at the reflux temperature for 30 minutes. The methyl alcohol was removed by evaporation under reduced pressure and the residue partitioned between dilute hydrochloric acid (20 ml of a 0.1N solution) and ether (20 ml). The ethereal phase was separated, washed with saturated sodium bicarbonate solution and with water and then dried over anhydrous magnesium sulphate. After evaporation of the ether under reduced pressure the product was distilled in a Kugelrohr apparatus to yield 3-methyl-2,4,5,6-tetrafluorobenzyl alcohol (1.2 g)--approximate b.p. 100° C./14 mm Hg.

Workup

  1. temperatureafter which the mixture was heated at the reflux temperature for 30 minutes
  2. customThe methyl alcohol was removed by evaporation under reduced pressure
  3. customthe residue partitioned between dilute hydrochloric acid (20 ml of a 0.1N solution) and ether (20 ml)
  4. customThe ethereal phase was separated
  5. washwashed with saturated sodium bicarbonate solution and with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customAfter evaporation of the ether under reduced pressure the product
  8. distillationwas distilled in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-7a0341657020433ea1fff5fd0d14e82c
Source dataset
uspto-grants-1985_11
Patent number
US04551546

Reaction notes

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