Propylene Chlorohydrin → 2-Chloropropyl 3-oxobutanoate

HRID 2418254Notes

Reaction equation

HRID 2418254 reaction equation
C([O-])(=O)C.[Na+].[Cl:6][CH:7]([CH3:10])[CH2:8][OH:9].[CH2:11]=[C:12]1[O:16][C:14](=[O:15])[CH2:13]1>>[C:14]([O:9][CH2:8][CH:7]([Cl:6])[CH3:10])(=[O:15])[CH2:13][C:12]([CH3:11])=[O:16]

Participants

4

Reactant 3

HCID 6566Propylene ChlorohydrinHCID 12661DiketeneHCID 517045Sodium Acetate

Product 1

HCID 132313652-Chloropropyl 3-oxobutanoateYield 69.2%

Procedure

0.7 g of sodium acetate was added to 7.5 g of 2-chloropropanol, to which 7.4 g of diketene was added dropwise with stirring while the reaction temperature was maintained at 40°-50° C. The reaction mixture was stirred at room temperature for an additional 2 hours and then worked up in the manner described in Referential Example 4. The resulting crude product was purified by distillation to obtain 9.8 g of 2-chloropropyl acetoacetate.

Workup

  1. additionwas added dropwise
  2. temperaturewas maintained at 40°-50° C
  3. stirringThe reaction mixture was stirred at room temperature for an additional 2 hours
  4. distillationThe resulting crude product was purified by distillation

Sources & evidence

ORD record
ord-871991d30cb346dc9724af0ddef45cb8
Source dataset
uspto-grants-1984_09
Patent number
US04472411

Reaction notes

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