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

HRID 2371292Notes

Reaction equation

HRID 2371292 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:12])[CH3:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 137990Methyl 4-acetylbenzoateHCID 4311764Sodium borohydride

Product 1

HCID 586417Methyl 4-(1-hydroxyethyl)benzoateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-Acetyl-benzoic acid methyl ester (5.0 g, 28.06 mmol) in MeOH (25 mL) at 0° C., was added sodium borohydride (NaBH4) (2.12 g, 56.12 mmol), the reaction mixture was stirred at rt for 3 h. The solvent was removed under reduced pressure, was diluted with H2O, the reaction mixture was extracted with ethyl acetate (150 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude product was dried under vacuum for 3 h to afford 4-(1-hydroxy-ethyl)-benzoic acid methyl ester (4.9 g, 99%): 1H NMR (300 MHz, CDCl3): δ 8.0 (d, J=7.8 Hz, 2H), 7.47 (d, J=8.1 Hz, 2H), 5.20 (q, J=6.9 Hz, 1H), 3.91 (s, 3H), 2.02 (d, J=7.2, Hz, 3H). TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate-hexanes (1:2); Rf=0.5.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionwas diluted with H2O
  3. extractionthe reaction mixture was extracted with ethyl acetate (150 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. dry with materialThe crude product was dried under vacuum for 3 h

Sources & evidence

ORD record
ord-8d838a85d1f743a0aee617dd7affcaf8
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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