Hydrochloric Acid → Methyl 4-methoxy-2-acetonyl-2-methylacetoacetate

HRID 329807Notes

Reaction equation

HRID 329807 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9][C:10](=[O:17])[CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13].Cl[CH2:19][C:20](=[O:22])[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:17])[C:11]([CH2:19][C:20]([CH3:21])=[O:22])([CH3:16])[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 11084163Methyl 4-methoxy-2-methylacetoacetate

Product 1

HCID 19871657Methyl 4-methoxy-2-acetonyl-2-methylacetoacetateYield 38.4%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

1.66 g (12 mmol) of potassium carbonate and 0.04 g (0.2 mmol) of benzyltriethylammonium chloride are suspended in 5 ml of acetonitrile. While stirring there are added thereto 1.60 g (10 mmol) of methyl 4-methoxy-2-methylacetoacetate and there are then added dropwise thereto within 15 minutes 1.39 g (15 mmol) of chloroacetone. The mixture is stirred at 20°-25° C. for a further 21 hours. The reaction mixture is poured into 20 ml of 2N HCl (pH value=1) and extracted 3 times with 20 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulphate and evaporated on a rotary evaporator. The crude product distils at 95° C./0.03 mbar. There results 0.83 g (38.4%) of methyl 4-methoxy-2-acetonyl-2-methylacetoacetate.

Workup

  1. additionare added
  2. stirringThe mixture is stirred at 20°-25° C. for a further 21 hours
  3. extractionextracted 3 times with 20 ml of ethyl acetate each time
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customevaporated on a rotary evaporator
  6. customThe crude product distils at 95° C./0.03 mbar

Sources & evidence

ORD record
ord-f1f5cb04d72e48e881240abdc0ad3af2
Source dataset
uspto-grants-1990_01
Patent number
US04892966

Reaction notes

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