Acetic Anhydride → 22012-59-5

HRID 1899860Notes

Reaction equation

HRID 1899860 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10](OC(=O)C)(=[O:12])[CH3:11]>[OH-].[Na+]>[C:10]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH3:9])[CH:4]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 728574-Bromo-m-cresol

Product 1

HCID 1457234122012-59-5

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A stirred mixture of 4-bromo-3-methylphenol (184.1 g) and aqueous NaOH (850 ml, 2M) at 20° C. is treated with acetic anhydride (136 ml) and stirred at room temperature for 1 h. The suspension is extracted with diethyl ether (3×300 ml) and the combined extracts are washed with aqueous NaOH (2×100 ml 2M), dried (Na2SO4) and filtered. The solvent is evaporated off under reduced pressure to yield the title compound as an oil.

Workup

  1. extractionThe suspension is extracted with diethyl ether (3×300 ml)
  2. washthe combined extracts are washed with aqueous NaOH (2×100 ml 2M)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-1c8bb0ab62ec48009c32ab6278473a1d
Source dataset
uspto-grants-1996_11
Patent number
US05574049

Reaction notes

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