Acetic Acid → 3-(2-Chlorophenyl)-2-oxopropyl Acetate

Reaction equation

[C:1]([O:4][CH2:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11](Cl)=[C:10](Cl)[CH:9]=1)(=[O:3])[CH3:2].[Cl:17]CC(=O)CC1C=CC=CC=1Cl.C(O)(=O)C.C(N(CC)CC)C>>[C:1]([O:4][CH2:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:17])(=[O:3])[CH3:2]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 8471Triethylamine

HCID 161000723-(3,4-Dichlorophenyl)-2-oxopropyl Acetate

HCID 161002051-Chloro-3-(2-chlorophenyl)propan-2-one

Product 1

HCID 161000603-(2-Chlorophenyl)-2-oxopropyl AcetateYield 43%

Procedure

The procedure described above for the synthesis of 3-(3,4-dichlorophenyl)-2-oxopropyl acetate was followed, reacting 1-chloro-3-(2-chlorophenyl)propan-2-one (0.556 g, 2.74 mmol) with acetic acid (0.31 mL, 0.33 g, 5.5 mmol) and triethylamine (0.76 mL, 0.56 g, 5.5 mmol). Flash chromatography over silica gel (5-40% ethyl acetate in hexanes) gave pure product (0.251 g, 43% yield): 1H NMR (400 MHz, CDCl3) δ 2.17 (s, 3H) 3.88 (s, 2H) 4.75 (s, 2H) 7.24-7.27 (m, 3H) 7.38-7.42 (m, 1H).