Hydrochloric Acid → Methyl 2-chloroacetoacetate

HRID 1380641Notes

Reaction equation

HRID 1380641 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[C:6](=[O:14])[O:7][C:8](C)(C)[O:9][C:10]=1[CH3:11].Cl>CO>[CH3:8][O:7][C:6](=[O:14])[CH:5]([Cl:4])[C:10]([CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 135878355-Chloro-2,2,6-Trimethyl-1,3-Dioxin-4-One

Product 1

HCID 107332Methyl 2-chloroacetoacetateYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 25% sodium methoxide in methanol (5 ml, 21.6 mmol) was added to a solution of 5-chloro-2,2,6-trimethyl-4H-1,3-dioxin-4-one (3.24 g, 18.4 mmol) in 10 ml of methanol at 20° C. The resulting yellow solution was stirred for 10 minutes, acidified with 10% HCl, and extracted with ether. Evaporation of the ether provided 2.35 g (94% yield, NMR assay ~90%) of a pale yellow oil, which was distilled to provide 1.8 g (66%) of pure title compound as a colorless liquid.

Workup

  1. extractionextracted with ether
  2. customEvaporation of the ether
  3. customprovided 2.35 g (94% yield, NMR assay ~90%) of a pale yellow oil, which
  4. distillationwas distilled

Sources & evidence

ORD record
ord-ef2a3cc275c1462c947e63131a5a7e6f
Source dataset
uspto-grants-1986_04
Patent number
US04582913

Reaction notes

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