Acetic Anhydride → Acetic acid 2-[3-(2-hydroxy-ethyl)-phenyl]-ethyl ester

HRID 521528Notes

Reaction equation

HRID 521528 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(#N)C>[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 100807412-[3-(2-Hydroxyethyl)phenyl]ethanol

Product 1

HCID 67076325Acetic acid 2-[3-(2-hydroxy-ethyl)-phenyl]-ethyl esterYield 41.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[3-(2-Hydroxy-ethyl)-phenyl]-ethanol (2.49 g, 15.0 mmol) was dissolved in ACN (5 ml) and acetic anhydride (3.06 g, 30 mmol) added. The mixture was stirred under reflux for 1 h and then evaporated to dryness. Silica gel chromatography (HEP/EA gradient) of the residue yielded 1.30 g of the title compound (mono-acetylated product).

Workup

  1. temperatureunder reflux for 1 h
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-0a04cf3d348c4d6f8e8f7199c4080f55
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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