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

HRID 521511

Reaction equation

HRID 521511 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-1eee8947a8e040e8a10209160bf2a857
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Linked notes

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