Methanol → 3,4-Dipropoxybenzyl alcohol

HRID 1169461Notes

Reaction equation

HRID 1169461 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH3:16])[CH:8]=[O:9])[CH2:2][CH3:3].CO.[BH4-].[Na+]>O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH3:16])[CH2:8][OH:9])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 41464793,4-DipropoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 178239893,4-Dipropoxybenzyl alcoholYield 92.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 3,4-dipropoxybenzaldehyde (6.65 g) and methanol (90 ml) was added sodium borohydride (1.13 g) at 0° C. The resulting mixture was stirred at 0° C. for 30 minutes. The reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 3,4-dipropoxybenzyl alcohol (6.22 g) as a yellow oily substance.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialwas dried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-46d3b4ab8f3c4e38b91828291461ca7b
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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