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

HRID 842080Notes

Reaction equation

HRID 842080 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+]>C(O)C.O>[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

5

Reactant 2

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 111387063-Cyclopentyloxy-4-methoxybenzyl alcoholYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (38 g 0.17 mol) in 40 ml of ethanol and sodium borohydride (1.63 g, 0.043 mol) was stirred for 2 hours at room temperature at which time the reaction was complete by TLC. The reaction was diluted with water and extracted with ethyl acetate. Evaporation of the ethyl acetate afforded 3-cyclopentyloxy-4-methoxybenzyl alcohol (37 g, 98%) suitable for the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-76d21c5a3ee841218c48652362c01637
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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