Acetoacetanilide → 3-Oxy-2-chlorobutanoic acid anylide

HRID 1756875Notes

Reaction equation

HRID 1756875 reaction equation
[C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Cl:14]Cl>C1(C)C=CC=CC=1.O>[Cl:14][CH:2]([C:3]([CH3:5])=[O:4])[C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

5

Reactant 2

HCID 7592AcetoacetanilideHCID 24526Chlorine2×

Product 1

HCID 1602123-Oxy-2-chlorobutanoic acid anylideYield 63.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
6 °C

Procedure

A suspension of 177 g (1.0 mole) of acetoacetanilide in 1440 ml of toluene and 167 ml of water, in a chlorinator (2000 ml 3-neck flask), was cooled to approximately 6° C. and chlorine gas was added at about the rate of 1.5 g/minute, while maintaining the temperature at 6° C. until 82.6 g (1.16 moles) of chlorine had been added (about 56 minutes). The resultant mixture was stirred for an additional 36 minutes and then heated to 70° C. for 15 minutes. The mixture was then cooled and the product was precipitated. The precipitate was filtered from the toluene/aqueous HCl mixture to give 134.8 g (63.9%) of α-chloroacetoacetanilide, mp 132°-134° C.

Workup

  1. additionhad been added (about 56 minutes)
  2. temperatureheated to 70° C. for 15 minutes
  3. temperatureThe mixture was then cooled
  4. customthe product was precipitated
  5. filtrationThe precipitate was filtered from the toluene/aqueous HCl mixture

Sources & evidence

ORD record
ord-378434176589414eb5f70b8ec9be1980
Source dataset
uspto-grants-1995_08
Patent number
US05442115

Reaction notes

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