Sodium borohydride → 5-Benzyloxy-2-methoxybenzyl alcohol

HRID 35292Notes

Reaction equation

HRID 35292 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:17][CH3:18])=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:17][CH3:18])=[C:13]([CH:16]=1)[CH2:14][OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 109666945-(Benzyloxy)-2-methoxybenzaldehyde

Product 1

HCID 143331325-Benzyloxy-2-methoxybenzyl alcoholYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Benzyloxy-2-methoxybenzaldehyde (150.4 g) was suspended in methanol (600 ml) and to the gently warmed stirred mixture was added, in portions, sodium borohydride (15.0 g). The methanol was evaporated and the residue partitioned between dichloromethane and water. The organic layer was washed with water, then saturated sodium chloride, dried with anhydrous magnesium sulphate and evaporated to dryness. The residue crystallised from dichloromethane/petroleum spirit (40°-60° ) to give 5-benzyloxy-2-methoxybenzyl alcohol (143.8 g, 95%), m.p. 50°-51°.

Workup

  1. temperatureto the gently warmed
  2. customThe methanol was evaporated
  3. customthe residue partitioned between dichloromethane and water
  4. washThe organic layer was washed with water
  5. dry with materialsaturated sodium chloride, dried with anhydrous magnesium sulphate
  6. customevaporated to dryness
  7. customThe residue crystallised from dichloromethane/petroleum spirit (40°-60° )

Sources & evidence

ORD record
ord-91b15ab66d5f401eb351dbea3663074b
Source dataset
uspto-grants-1988_08
Patent number
US04766121

Reaction notes

Loading…