Acetic Acid → 3-(3,4-Dichlorophenyl)-2-oxopropyl Acetate

HRID 2375559Notes

Reaction equation

HRID 2375559 reaction equation
Cl[CH2:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1.[C:14]([OH:17])(=[O:16])[CH3:15].C(N(CC)CC)C>CC(C)=O>[C:14]([O:17][CH2:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 161001771-Chloro-3-(3,4-dichlorophenyl)propan-2-one

Product 1

HCID 161000723-(3,4-Dichlorophenyl)-2-oxopropyl AcetateYield 33.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a round-bottomed flask, 1-chloro-3-(3,4-dichlorophenyl)propan-2-one (0.545 g, 2.30 mmol) was taken up in 2 mL acetone, and acetic acid (0.26 mL, 0.28 g, 4.6 mmol) was added. The solution was cooled in an ice water bath, and triethylamine (0.64 mL, 0.47 g, 4.6 mmol) added dropwise via syringe over 30 minutes. The reaction mixture was then stirred overnight. Precipitated triethylammonium chloride was removed by filtration, and the filtrate was evaporated, taken up in 10 mL ethyl acetate, washed twice with brine, dried over anhydrous MgSO4, filtered, and evaporated. The crude product was purified by flash chromatography over silica gel (10-30% ethyl acetate in hexanes) to give a pure product (0.200 g, 33% yield): 1H NMR (400 MHz, CDCl3) δ 2.17 (s, 3H) 3.71 (s, 2H) 4.71 (s, 2H) 7.05 (dd, J=8.2, 2.2 Hz, 1H) 7.32 (d, J=2.0 Hz, 1H) 7.41 (d, J=8.1 Hz, 1H).

Workup

  1. temperatureThe solution was cooled in an ice water bath
  2. customPrecipitated triethylammonium chloride was removed by filtration
  3. customthe filtrate was evaporated
  4. washwashed twice with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography over silica gel (10-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e687a1af1f474356b9e9484effc370a7
Source dataset
uspto-grants-2008_12
Patent number
US07465798B2

Reaction notes

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