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

HRID 1671638

Reaction equation

HRID 1671638 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 10 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-b0844c52f9f74dd8bc2b36582ae2969f
Source dataset
uspto-grants-2011_08
Patent number
US07994333B2

Linked notes

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