Ammonia → Methyl 3-oxohexanoate

77.8 g (1.05 mol) of calcium hydroxide were placed in 550 ml of methylene chloride, and 116 g (1.0 mol) of methyl acetoacetate were added dropwise at 20° to 30° C. over 20 minutes, with vigorous stirring. Stirring was then continued for half an hour. 122.6 g (1.15 mol) of butyryl chloride were then metered into the thick suspension at a temperature of 30° to 35° C. over 1.5 hours. Stirring was then continued for 2 hours at 40° C. 56.2 g (1.05 mol) of ammonium chloride in 350 ml of water were then added to the reaction mixture at 30° C. and the resulting mixture was stirred for half an hour. After the pH had been adjusted to 8.9-9.0 by the addition of aqueous ammonia, the mixture was stirred for a further 3 hours at 30° to 35° C. The reaction mixture was then acidified with concentrated hydrochloric acid (pH 0.5-1.0) and washed with sodium bicarbonate solution and water. After separation of the aqueous phase, the methylene chloride was distilled off on an evaporator. This gave 134 g (GC purity 84%) of methyl butyrylacetate as a yellowish liquid (yield 78%).

1. waitwas then continued for half an hour
2. stirringStirring
3. stirringthe resulting mixture was stirred for half an hour
4. stirringthe mixture was stirred for a further 3 hours at 30° to 35° C
5. washwashed with sodium bicarbonate solution and water
6. customAfter separation of the aqueous phase
7. distillationthe methylene chloride was distilled off on an evaporator

ORD record

ord-5ddd91ade2894a2bbdcb304634401fca

Source dataset

uspto-grants-1993_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05194671