Methyl 4-acetylbenzoate → Methyl 4-(1-hydroxyethyl)benzoate

HRID 1500997Notes

Reaction equation

HRID 1500997 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 137990Methyl 4-acetylbenzoateHCID 4311764Sodium borohydride

Product 1

HCID 586417Methyl 4-(1-hydroxyethyl)benzoateYield 85.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 4-acetylbenzoate (1.78 g, 10 mmol) in ethanol (100 mL) was added sodium borohydride (0.76 g, 20 mmol) in portions at 0° C. The mixture was stirred for 30 minutes and warmed to 20° C. Then the mixture was stirred at the same temperature for 12 hours. After that, the mixture was concentrated in vacuo to give methyl 4-(1-hydroxyethyl)benzoate (1.54 g, 85%).

Workup

  1. stirringThen the mixture was stirred at the same temperature for 12 hours
  2. concentrationAfter that, the mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-8cd39273f3e24f4184dad13be3a5185f
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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