Hydrochloric Acid → Methyl 4-methoxy-2-(2-oxobutyl)-acetoacetate

HRID 329812Notes

Reaction equation

HRID 329812 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:22])[CH2:20][CH3:21].Cl>[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](=[O:22])[CH2:20][CH3:21])[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 69219Chloromethyl ethyl ketoneHCID 123500Methyl 4-methoxyacetoacetate

Product 1

HCID 19871666Methyl 4-methoxy-2-(2-oxobutyl)-acetoacetateYield 55.3%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

67.99 g (492 mmol) of potassium carbonate and 1.87 g (8.2 mmol) of benzyltriethylammonium chloride are suspended in 500 ml of acetonitrile. 59.86 g (410 mmol) of methyl 4-methoxyacetoacetate are added thereto while stirring. 65.50 g (615 mmol) of 1-chloro-2-butanone are added dropwise thereto within 30 minutes and the mixture is stirred at 20°-25° C. for 23 hours. The reaction mixture is poured into 1 l of 1N HCl (pH value=1) and extracted 3 times with 700 ml of ethyl acetate each time. The combined organic phases are dried over magnesium sulphate and concentrated on a rotary evaporator. The crude product distils at 115° C./0.05 mbar. There results 49.01 g (55.3%) of methyl 4-methoxy-2-(2-oxobutyl)-acetoacetate.

Workup

  1. stirringthe mixture is stirred at 20°-25° C. for 23 hours
  2. extractionextracted 3 times with 700 ml of ethyl acetate each time
  3. dry with materialThe combined organic phases are dried over magnesium sulphate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe crude product distils at 115° C./0.05 mbar

Sources & evidence

ORD record
ord-c2d9b271073d4816982f12d4f1820928
Source dataset
uspto-grants-1990_01
Patent number
US04892966

Reaction notes

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