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

HRID 1597294Notes

Reaction equation

HRID 1597294 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

Conditions

Temperature
18.5 °C

Procedure

To a solution of 48.70 g (220 mmoles) or 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. customAfter a further 20 min the methanol was removed in vacuo
  2. customThe ether phase was evaporated to dryness

Sources & evidence

ORD record
ord-2e7bbcb8efd840cca3b42edbdc7b2303
Source dataset
uspto-grants-2001_09
Patent number
US06294541B1

Reaction notes

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