Sodium borohydride → 4-Methoxy-3-(3-methoxypropoxy)benzenemethanol

HRID 2258290Notes

Reaction equation

HRID 2258290 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18]>CO>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[O:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 112183584-Methoxy-3-(3-methoxypropoxy)benzaldehyde

Product 1

HCID 451081634-Methoxy-3-(3-methoxypropoxy)benzenemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (39.7 g) is added in portions to a solution of 4-methoxy-3-(3-methoxypropoxy)-benzaldehyde (336 g) in methanol (3.36 liters), the reaction temperature being maintained at 0°-5° C. When the addition is complete, the batch is stirred for a further 60 minutes at room temperature and concentrated under reduced pressure, and the residue is partitioned between ice-cooled 2N hydrochloric acid and ethyl acetate (3×2 liters). The combined organic phases are washed with water and saturated sodium hydrogen carbonate solution, added over magnesium sulfate and concentrated. Purification of the residue by FC on silica gel (dichloromethane/methanol 96:4) yields the title compound in the form of an oil (326 g): Rf (ethyl acetate/hexane 2:1)=0.31. Anal. C12H18O4 (226.27): calc. C, 63.70; H, 8.02; found C, 63.70; H, 8.24.

Workup

  1. temperaturethe reaction temperature being maintained at 0°-5° C
  2. additionWhen the addition
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is partitioned between ice-
  5. temperaturecooled 2N hydrochloric acid and ethyl acetate (3×2 liters)
  6. washThe combined organic phases are washed with water and saturated sodium hydrogen carbonate solution
  7. additionadded over magnesium sulfate
  8. concentrationconcentrated
  9. customPurification of the residue by FC on silica gel (dichloromethane/methanol 96:4)

Sources & evidence

ORD record
ord-83042ae57f984dd386f82d713aac3a86
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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