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

HRID 1755187Notes

Reaction equation

HRID 1755187 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); R1=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-a2150d4cb92c4c7a89fa22367af689c8
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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