Acetyl chloride → 4-Methoxyphenyl acetate

HRID 2097587Notes

Reaction equation

HRID 2097587 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[C:17](Cl)(=[O:19])[CH3:18]>CCOCC>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 90154-Methoxyphenol

Product 1

HCID 709874-Methoxyphenyl acetateYield 107.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethylamine (14.55 mL, 104.43 mmol) was added to an ice-bath cooled solution of 4-methoxyphenol (5.185 g, 41.77 mmol) in anhydrous ether (200 mL) under nitrogen atmosphere. Acetyl chloride (5.94 mL, 83.53 mmol) was added drop-wise and reaction mixture then allowed to warm to room temperature and stir for a further 10 min. The reaction mixture was partitioned between ethyl acetate and sat aqueous sodium bicarbonate solution. The phases were separated and the organic phase was dried over sodium sulphate, filtered and filtrate solvents removed in vacuo to afford the title compound (7.45 g, quant) as a brown liquid.

Workup

  1. customdrop-wise and reaction mixture
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. customfiltrate solvents removed in vacuo

Sources & evidence

ORD record
ord-97fde847ebf8486e96e7bd1c13355d29
Source dataset
uspto-grants-2013_05
Patent number
US08450346B2

Reaction notes

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