Acetyl chloride → 4-Fluoro-3-methylphenyl acetate

HRID 510908Notes

Reaction equation

HRID 510908 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>C(Cl)Cl>[C:17]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH3:9])[CH:4]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 27373944-Fluoro-3-methylphenol

Product 1

HCID 679691964-Fluoro-3-methylphenyl acetateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-fluoro-3-methylphenol (3.0 g, 23 mmol) and methylene chloride (96 mL) was cooled to 0° C. in an ice bath. Triethylamine (4.9 mL, 35 mmol) was introduced to the solution followed by dropwise addition of acetyl chloride (2.3 mL, 33 mmol). The ice bath was removed and the mixture was stirred for 1 hour. The mixture was then extracted with methylene chloride and washed with 0.5 N HCl, saturated sodium bicarbonate and brine. The extracts were dried over sodium sulfate, filtered and evaporated to give 4-fluoro-3-methylphenyl acetate (3.9 g, quantitative). 1H NMR (400 MHz, CDCl3): δ 7.00 (m, 1H), 6.87 (m, 2H), 2.29 (m, 6H).

Workup

  1. customThe ice bath was removed
  2. extractionThe mixture was then extracted with methylene chloride
  3. washwashed with 0.5 N HCl, saturated sodium bicarbonate and brine
  4. dry with materialThe extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-43e48d2b1ae14d639d1caaac4ef8ae6f
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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