Sulfuryl chloride → Ethyl 2-chloro-2-(o-methylbenzyl)-acetoacetate

HRID 973920Notes

Reaction equation

HRID 973920 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][C:7]1[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=1[CH2:9][CH:10]([C:16]([CH3:18])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>>[Cl:4][C:10]([CH2:9][C:8]1[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=1[CH3:6])([C:16]([CH3:18])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 15588514Ethyl 2-(2-methylbenzyl)-3-oxobutanoate

Product 1

HCID 19987140Ethyl 2-chloro-2-(o-methylbenzyl)-acetoacetate

Procedure

325 g (2.4 moles) of sulfuryl chloride were added dropwise to 511.0 g (2.2 moles) of ethyl 2-(o-methylbenzyl)-acetoacetate in the course of 2 hours, while stirring. Thereafter, the mixture was heated at 50° to 55° C. for 4 hours. The crude product was purified by vacuum distillation without a column. 547 g (92% of the theoretical yield) of ethyl 2-chloro-2-(o-methylbenzyl)-acetoacetate of boiling point 120° C. at 0.01 mm Hg were obtained.

Workup

  1. temperatureThereafter, the mixture was heated at 50° to 55° C. for 4 hours
  2. distillationThe crude product was purified by vacuum distillation without a column

Sources & evidence

ORD record
ord-cd5475efabf04a52b58633643adbe3cb
Source dataset
uspto-grants-1991_11
Patent number
US05066640

Reaction notes

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