Sulfuryl chloride → Methyl 2-chloro-3-oxo-3-(p-methoxyphenyl)propionate

HRID 1590544Notes

Reaction equation

HRID 1590544 reaction equation
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].S(Cl)([Cl:19])(=O)=O>ClC(Cl)(Cl)Cl>[Cl:19][CH:3]([C:2](=[O:1])[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 2759699Methyl 4-methoxy-beta-oxobenzenepropanoate

Product 1

HCID 10014646Methyl 2-chloro-3-oxo-3-(p-methoxyphenyl)propionateYield 91.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

131 g of the methyl 3-oxo-3-(p-methoxyphenyl)propionate obtained in the above (1) was dissolved in 1.3 l of tetrachloromethane, and to the solution was added dropwise 85 g of sulfuryl chloride at 45° to 50° C. over 1 hour. After the dropwise addition, the mixture was stirred at the same temperature for 1 hour, cooled, washed with water and dried. Subsequently, the oily product of the residue obtained by evaporation of the solvent was distilled under reduced pressure to obtain 140 g of methyl 2-chloro-3-oxo-3-(p-methoxyphenyl)propionate.

Workup

  1. additionAfter the dropwise addition
  2. temperaturecooled
  3. washwashed with water
  4. customdried
  5. customSubsequently, the oily product of the residue obtained by evaporation of the solvent
  6. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-c9f670e3e219400c9f5c3831866b0c2e
Source dataset
uspto-grants-1993_04
Patent number
US05204248

Reaction notes

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