2-Chloroacetophenone → HCID 12664904, compound

HRID 349720Notes

Reaction equation

HRID 349720 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]([O-])(=[S:13])[CH3:12].[K+]>CC(C)=O>[C:11]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4])(=[S:13])[CH3:12]

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 23670855Potassium ethanethioate

Product 1

HCID 12664904HCID 12664904, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloroacetophenone in acetone (3.10 g, 200 ml) was added potassium thioacetate (2.80 g, 1.2 equivalents) and the reaction mixture was stirred overnight at RT. The salt precipitate was filtered off and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel to give 2.04 g of α-thioacetyl acetophenone as orange reddish oil. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 7.98–8.02 (2 H, m) 7.60 (1 H, t, J=7.48 Hz) 7.48 (2 H, t, J=7.78 Hz) 4.40 (2 H, s) 2.41 (3 H, s). MS [ESI, MNa+] m/z calcd for C10H10O2SNa 217.04, found 217.16.

Workup

  1. filtrationThe salt precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-206fed69242048efa66e90f5e5608284
Source dataset
uspto-grants-2007_02
Patent number
US07179926B2

Reaction notes

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