Acetic Anhydride → HCID 54261822, compound

HRID 1417559Notes

Reaction equation

HRID 1417559 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([CH3:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:14](OC(=O)C)(=[O:16])[CH3:15].O.O.O.C([O-])(=O)C.[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]([C:14](=[O:16])[CH3:15])[C:11](=[O:12])[CH3:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 1869927193484-84-5HCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 54261822HCID 54261822, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-(3-bromo-4-methoxyphenyl)acetone (410 mg, 1.69 mmol), acetic anhydride (0.318 mL, 344 mg, 3.37 mmol), and p-toluenesulfonic acid (12.7 mg, 0.067 mmol) was stirred for 30 min. at RT. Boron trifluoride-acetic acid complex (0.275 mL, 372 mg, 2.92 mmol) was added and stirring was continued for 20 h. Sodium acetate trihydrate (919 mg, 6.76 mmol) in 1.7 mL of water was added and the mixture was refluxed for 3 h. Upon cooling, the reaction was partitioned between 50 mL of ethyl acetate and 30 mL of saturated aqueous sodium bicarbonate. The layers were separated and the organic layer was washed with 30 mL of brine. Drying over sodium sulfate and evaporation provided 450 mg of crude product. Purification by flash column chromatography, eluting with 10% ethyl ether in hexane, gave the 234 mg of the title compound as pale crystals. Mass spectrum (NH3/CI): m/z=285.0 (M+1).

Workup

  1. additionBoron trifluoride-acetic acid complex (0.275 mL, 372 mg, 2.92 mmol) was added
  2. stirringstirring
  3. waitwas continued for 20 h
  4. temperaturethe mixture was refluxed for 3 h
  5. temperatureUpon cooling
  6. customthe reaction was partitioned between 50 mL of ethyl acetate and 30 mL of saturated aqueous sodium bicarbonate
  7. customThe layers were separated
  8. washthe organic layer was washed with 30 mL of brine
  9. dry with materialDrying over sodium sulfate and evaporation
  10. customprovided 450 mg of crude product
  11. customPurification by flash column chromatography
  12. washeluting with 10% ethyl ether in hexane

Sources & evidence

ORD record
ord-1957016c23e948ce90c903565e7aaf52
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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