Acetyl chloride → Ethyl 2-acetylacetoacetate

HRID 1375100Notes

Reaction equation

HRID 1375100 reaction equation
[Na].[C:2]([O:8][CH2:9][CH3:10])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].[C:11](Cl)(=[O:13])[CH3:12]>C1(C)C=CC=CC=1>[C:4]([CH:3]([C:11](=[O:13])[CH3:12])[C:2]([O:8][CH2:9][CH3:10])=[O:7])(=[O:5])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8868Ethyl AcetoacetateHCID 5360545Sodium

Product 1

HCID 79063Ethyl 2-acetylacetoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

5 g of sodium salt of ethyl acetoacetate was mixed with 30 ml of toluene. Over 20 minutes, 5 g of acetic acid chloride was added dropwise, and the mixture was stirred for one hour at room temperature and at 85° C. for 3 hours. The solid was filtered off and washed with diethyl ether. Fractional distillation of the liquid phase yielded ethyl 2-acetyl-3-oxo-butyrate.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with diethyl ether
  3. distillationFractional distillation of the liquid phase

Sources & evidence

ORD record
ord-7048be1d1a804a55b9da8795a3953252
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

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