Methyl chloroacetate → HCID 14911858, compound

HRID 1375103Notes

Reaction equation

HRID 1375103 reaction equation
C[C:2]([O-:5])([CH3:4])C.[K+].[CH2:7]([O:9][C:10](=[O:15])[CH2:11][C:12]([CH3:14])=[O:13])[CH3:8].[CH3:16][O:17][C:18](=[O:21])[CH2:19]Cl.C[C:23](N(C)C)=[O:24]>>[CH3:23][O:24][C:2](=[O:5])[CH2:4][C:11]([C:12](=[O:13])[CH3:14])([C:10]([O:9][CH2:7][CH3:8])=[O:15])[CH2:19][C:18]([O:17][CH3:16])=[O:21]

Participants

5

Reactant 4

HCID 7295Methyl chloroacetate2×HCID 8868Ethyl AcetoacetateHCID 31374DimethylacetamideHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 14911858HCID 14911858, compound

Procedure

86 g of potassium tert-butylate was dissolved in 150 ml of dimethyl acetamide and 100 g of acetoacetic acid ethyl ester was added drop by drop with stirring. Subsequently, 83 g of chloroacetic acid methyl ester was added dropwise. When the exothermic reaction ended, 5 g of potassium tert-butylate and 5 g of chloroacetic acid methyl ester were added alternately until conversion was complete. The solid was filtered off and washed with ethyl acetate. Fractional distillation yielded 30 g of 3-acetyl-3-(ethoxycarbonyl)-pentanedioic acid dimethyl ester (purity: 91%; colorless).

Workup

  1. customWhen the exothermic reaction
  2. filtrationThe solid was filtered off
  3. washwashed with ethyl acetate
  4. distillationFractional distillation

Sources & evidence

ORD record
ord-d32bb448c53b4521bedf32ef217c6b87
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

Loading…