Chloroacetone → HCID 10954610, compound

HRID 329799Notes

Reaction equation

HRID 329799 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9][C:10](=[O:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13].Cl[CH2:18][C:19](=[O:21])[CH3:20]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[CH3:7][O:8][CH2:9][C:10](=[O:16])[CH:11]([CH2:18][C:19]([CH3:20])=[O:21])[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 123500Methyl 4-methoxyacetoacetate

Product 1

HCID 10954610HCID 10954610, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

165.8 g (1.2 mol) of potassium carbonate and 4.6 g (0.02 mol) of benzyltriethylammonium chloride are suspended in 500 ml of acetonitrile. While stirring there are added thereto 146.1 g (1 mol) of methyl 4-methoxy-acetoacetate and there are added dropwise thereto within 10 minutes 138.8 g (1.5 mol) of chloroacetone. The mixture is stirred at 20°-25° C. for a further 7 hours. The reaction mixture is poured on to 1 liter of 10% NaH2PO4 solution/ice (pH value=5) and extracted 3 times with 500 ml of ethyl acetate each time. The combined organic phases are dried over magnesium sulphate and concentrated on a rotary evaporator to give 206.30 g (100%) of methyl 4-methoxy-2-acetonylacetoacetate, content: 84.3%; b.p. 104°-105° C./0.06 mbar.

Workup

  1. additionare added
  2. stirringThe mixture is stirred at 20°-25° C. for a further 7 hours
  3. extractionextracted 3 times with 500 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-755eece8e0da4a2a84a9e46ea03fa25e
Source dataset
uspto-grants-1990_01
Patent number
US04892966

Reaction notes

Loading…