3-Cyclopentyloxy-4-methoxybenzaldehyde → 3-Cyclopentyloxy-4-methoxybenzyl alcohol

HRID 2227345Notes

Reaction equation

HRID 2227345 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:10][OH:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 111387063-Cyclopentyloxy-4-methoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 48.70 g (220 mmoles) of 3-cyclopentyloxy-4-methoxybenzaldehyde in 250 ml of methanol was added portionwise 8.57 g (220 mmoles) of 97% sodium borohydride within 10 min at 15-22° C. under cooling. After a further 20 min the methanol was removed in vacuo and the residue taken up in 10 ml of water and 300 ml of ether. The ether phase was evaporated to dryness: 48.5 g (99.2%) of liquid benzyl alcohol.

Workup

  1. temperatureunder cooling
  2. customAfter a further 20 min the methanol was removed in vacuo
  3. customThe ether phase was evaporated to dryness

Sources & evidence

ORD record
ord-07cc4b0d0059463a9d0a43cd6515db10
Source dataset
uspto-grants-2002_07
Patent number
US06413975B1

Reaction notes

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