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

HRID 1810911Notes

Reaction equation

HRID 1810911 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])O.[Na+].[C:16](OC(=O)C)(=[O:18])[CH3:17]>O1CCOCC1.O>[OH:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([O:1][C:16](=[O:18])[CH3:17])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 834043-Hydroxyphenethyl alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 67076782Acetic acid 3-(2-hydroxy-ethyl)-phenyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(3-Hydroxyphenyl)ethanol (400 mg, 2.90 mmol) was dissolved in a mixture of 4 ml of dioxane and 4 ml of water, and sodium hydrogencarbonate (2.43 g, 29 mmol) was added followed by acetic anhydride (2.96 g, 29 mmol) with ice cooling. The mixture was stirred overnight at room temperature and then partitioned between 2 N hydrochloric acid and EA. The aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate and evaporated to dryness to yield the crude title compound which was used without further purification.

Workup

  1. additionwas added
  2. custompartitioned between 2 N hydrochloric acid and EA
  3. extractionThe aqueous phase was extracted with EA
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-850cd87663534ab8af2c944346ca6984
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

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