Sodium borohydride → 5-Benzyloxy-2-methoxybenzyl alcohol

HRID 1761618Notes

Reaction equation

HRID 1761618 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 reidue 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 reidue 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-306df501fcb4460e97a83c5d4237d650
Source dataset
uspto-grants-1989_05
Patent number
US04826876

Reaction notes

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