Benzyl Alcohol → Benzyl 3-hydroxybutanoate

HRID 1734508Notes

Reaction equation

HRID 1734508 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1(=[O:14])[O:13][CH:11]([CH3:12])[CH2:10]1.Cl>[OH-].[Na+]>[OH:13][CH:11]([CH3:12])[CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:14]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 18303beta-BUTYROLACTONE

Product 1

HCID 562226Benzyl 3-hydroxybutanoateYield 80.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideCatalyst

Conditions

Temperature
0 °C

Procedure

0.3 g of sodium hydroxide was added to 64.8 g of benzylalcohol and the reaction mixture was cooled to 0° C. To this reaction mixture was added 12.9 g of β-butyrolactone and the mixture was stirred for 5 minutes at 0° C. and for 2 hours at room temperature. After reaction, the reaction solution was neutralized by adding 15 ml of 1N-HCl solution and the separated organic layer was washed with saturated sodium bicarbonate aqueous solution and saline, and dried over magnesium sulfate. The resulting organic layer was distilled under reduced pressure to give 23.3 g (79%) of benzyl 3-hydroxybutanoate [Compound (11)]as oil.

Workup

  1. customAfter reaction
  2. washthe separated organic layer was washed with saturated sodium bicarbonate aqueous solution and saline
  3. dry with materialdried over magnesium sulfate
  4. distillationThe resulting organic layer was distilled under reduced pressure

Sources & evidence

ORD record
ord-54f916a9f11746a09a70ee9a0f8a01b1
Source dataset
uspto-grants-1996_07
Patent number
US05534510

Reaction notes

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