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

HRID 1995691Notes

Reaction equation

HRID 1995691 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 alcohol

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 0.1 N 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. N.m.r. (1H(ppm)CDCl3): 2.20 (s,3H); 3.20 (t,1H); 4.6 (m,2H) Infra red (liquid film): 3300, 1650, 1480, 1120, 1110 cm-1

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 0.1 N 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-40ef4ecce93b42e2ad84077901f265f1
Source dataset
uspto-grants-1983_09
Patent number
US04405640

Reaction notes

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