Acetic Acid → Acetic Acid 2-oxo-3-phenyl-propyl Ester

HRID 2375575Notes

Reaction equation

HRID 2375575 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C(N(CC)CC)C.Cl[C:13]1[CH:14]=[C:15]([CH2:20][C:21](=[O:23])[CH3:22])[CH:16]=[CH:17][C:18]=1Cl>>[O:23]=[C:21]([CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:13][CH:14]=1)[CH2:22][O:3][C:1](=[O:4])[CH3:2]

Participants

4

Reactant 3

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

Product 1

HCID 12222463Acetic Acid 2-oxo-3-phenyl-propyl EsterYield 33%

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 (10-30% ethyl acetate in hexanes) gave pure product (0.83 g, 33% yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 2.08 (s, 3H) 3.80 (s, 2H) 4.85 (s, 2H) 7.17-7.36 (m, 5H).

Sources & evidence

ORD record
ord-40acb545ea104779b210c3e79e8b4ca9
Source dataset
uspto-grants-2008_12
Patent number
US07465798B2

Reaction notes

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