Sodium borohydride → 5-Benzyloxy-2-methoxybenzyl alcohol

HRID 346333Notes

Reaction equation

HRID 346333 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-bfe7e8f168404fb7b3a520b6b55b9252
Source dataset
uspto-grants-1991_10
Patent number
US05061798

Reaction notes

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