Methanol → Methyl 4-(4-chlorophenyl)-4-oxobutanoate

HRID 22489Notes

Reaction equation

HRID 22489 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:18]=[CH:17][C:9]([C:10]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:11])=[CH:8][CH:7]=1.[CH3:19]O>>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([CH2:12][CH2:13][C:14]([O:16][CH3:19])=[O:15])=[O:11])=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 776043-(4-Chlorobenzoyl)propionic acid

Product 1

HCID 230774Methyl 4-(4-chlorophenyl)-4-oxobutanoateYield 97%

Procedure

Thionyl chloride (2.4 ml, 33 mmol) was added dropwise to a stirred solution of 3-(4-chlorobenzoyl)propionic acid (5.0 g, 24 mmol) in dry methanol (50 ml) at 0° C. The mixture was heated at reflux for 2 h, cooled and the solvent removed under reduced pressure to give methyl 3-(4-chlorobenzoyl)propionate (5.3 g, 97%) as a colourless oil. deltaH (250 MHz, CDCl3) 7.93 (2H, d, J 8.5 Hz), 7.45 (2H, d, J 8.6 Hz), 3.72 (3H, s), 3.29 (2H, t, J 6.6 Hz), 2.78 (2H, t, J 6.6 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-863af67d1d7f4f9899ecab0863d3604e
Source dataset
uspto-grants-1995_06
Patent number
US05428168

Reaction notes

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