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

HRID 327612Notes

Reaction equation

HRID 327612 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>[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 702EthanolSolvent

Procedure

To a stirred solution of 10.42 g (47.3 mmol) of 3-cyclopentoxy-4-methoxybenzaldehyde in 100 mL of absolute ethanol was added 0.9 g (23.8 mmol) of sodium borohydride in one portion. The mixture was stirred for 1 hour at room temperature after which time the reaction was quenched with excess acetic acid, concentrated and azeotroped to dryness three times with 25 mL portions of toluene. The residue was dissolved in 100 mL of chloroform, washed with two, 25 mL portions of saturated sodium chloride, dried over magnesium sulfate, and concentrated to dryness. Liquid chromatography of the crude oil over 200 g of silica gel with 10% ethyl acetate in hexane provided an analytically pure oil after drying in vacuo.

Workup

  1. customwas quenched with excess acetic acid
  2. concentrationconcentrated
  3. customazeotroped to dryness three times with 25 mL portions of toluene
  4. dissolutionThe residue was dissolved in 100 mL of chloroform
  5. washwashed with two, 25 mL portions of saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness
  8. customLiquid chromatography of the crude oil over 200 g of silica gel with 10% ethyl acetate in hexane provided an analytically pure oil
  9. customafter drying in vacuo

Sources & evidence

ORD record
ord-a9e5ea4e9f5c4ec4ad4d3df1f7062c26
Source dataset
uspto-grants-1993_12
Patent number
US05274002

Reaction notes

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