Acetic Acid → 4-Acetoxybenzyl alcohol

HRID 552048

Reaction equation

HRID 552048 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Na].C(O)(=O)C.O>CO>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 70144Benzaldehyde, 4-(acetyloxy)-HCID 5360545Sodium

Product 1

HCID 959064-Acetoxybenzyl alcoholYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 4-formylphenol acetate (6.0 g, 36.4 mmol) in 60 ml of methanol was added sodium boronhydride (1.50 g, 39.6 mmol) at 0° C. The resultant mixture was stirred for 1 hour, neutralized with acetic acid and then poured into water. The mixture was extracted three times with ether and the combined organic layer was dried over magnesium sulfate. After removal of solvent, the compound was purified by flash chromatography using heptane/ethyl acetate (80/20-70/30) as eluent in a yield of 41%.

Workup

  1. extractionThe mixture was extracted three times with ether
  2. dry with materialthe combined organic layer was dried over magnesium sulfate
  3. customAfter removal of solvent
  4. customthe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-7ed4229d57a94f0da113cdb9686b05a9
Source dataset
uspto-grants-2011_05
Patent number
US07951550B2

Linked notes

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