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

HRID 2375566Notes

Reaction equation

HRID 2375566 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C(N(CC)CC)C.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21](=[O:23])[CH3:22])[CH:16]=[CH:17][C:18]=1Cl>>[C:1]([O:4][CH2:22][C:21](=[O:23])[CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[CH:14]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 810603',4'-Dichloropropiophenone

Product 1

HCID 161000713-(3-Chlorophenyl)-2-oxopropyl AcetateYield 46%

Procedure

This crude material was reacted with acetic acid (1.42 mL, 1.49 g, 24.8 mmol) and triethylamine (3.46 mL, 2.51 g, 24.8 mmol), as described above for the synthesis of 3-(3,4-dichlorophenyl)propan-2-one. Flash chromatography over silica gel (20% ethyl acetate in hexanes) gave pure product (1.22 g, 46% yield): 1H NMR (400 MHz, CDCl3) δ 2.16 (s, 3H) 3.72 (s, 2H) 4.69-4.71 (m, 2H) 7.08-7.11 (m, 1H) 7.21-7.23 (m, 1H) 7.26-7.29 (m, 2H).

Sources & evidence

ORD record
ord-3b326d846f7d488397820cf9da10b162
Source dataset
uspto-grants-2008_12
Patent number
US07465798B2

Reaction notes

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