Methanol → 3,4-Diethoxybenzyl alcohol

HRID 1169503Notes

Reaction equation

HRID 1169503 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH:7]=[O:8])[CH3:2].CO.[BH4-].[Na+]>O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH2:7][OH:8])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 748473,4-DiethoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 8540533,4-Diethoxybenzyl alcoholYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 3,4-diethoxybenzaldehyde (6.68 g) and methanol (100 ml) was added sodium borohydride (1.30 g) at 0° C. The resulting mixture was stirred at 0° C. for 45 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 resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 3,4-diethoxybenzyl alcohol (6.64 g) as a yellow oil.

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 resulting organic layer was evaporated under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-5f8fa155e3e64a7bb4d8f6ea9166fbdd
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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