Methanol → 2-Methoxybenzyl alcohol

HRID 1034119Notes

Reaction equation

HRID 1034119 reaction equation
CO.[BH4-].[Na+].[CH3:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]>O>[CH3:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 86582-MethoxybenzaldehydeHCID 4311764Sodium borohydride2×

Product 1

HCID 691542-Methoxybenzyl alcoholYield 201.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Five milliliters of a methanol solution containing 0.6 g (16.0 mmol) of NaBH4 is added dropwise to 10 ml of a methanol solution containing 2.0 g (14 7 mmol) of 2-methoxybenzaldehyde, followed by stirring at room temperature for about 1 hour. After the progress of reaction has been confirmed by thin-layer chromatography, 100 ml of water is poured into the reaction solution to decompose excess NaBH4, followed by extraction with three 30 ml portions of ether. The ether layer is dried over anhydrous Na2SO4, and then filtered. When the solvent is removed by distillation, 1.95 g (yield: 96.1%) of 2-methoxybenzyl alcohol is obtained as an oily colorless product.

Workup

  1. customAfter the progress of reaction
  2. additionis poured into the reaction solution
  3. extractionfollowed by extraction with three 30 ml portions of ether
  4. dry with materialThe ether layer is dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customWhen the solvent is removed by distillation

Sources & evidence

ORD record
ord-34f9e93c668a4d839a9c6b08c4d32cf9
Source dataset
uspto-grants-1994_05
Patent number
US05314693

Reaction notes

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