Hydrochloric Acid → Heptanoic acid, 3-methyl-, 1-methylpropyl ester

Temperatur

5 °C

Several drops of a solution of 4.9 g of n-butyl bromide in 126 ml of dry diethyl ether were added to a suspension of 10.53 g of magnesium and a trace amount of iodine in 80 ml of dry diethyl ether, and the mixture was stirred vigorously. The colour of the iodine disappeared upon slight heating, and the rest of the n-butyl bromide solution was then added dropwise at a rate sufficient to maintain a constant reflux of the reaction mixture. After addition of the n-butyl bromide solution the reaction mixture was heated to reflux for a further 15 minutes and was then cooled to 5° C. with an ice-water bath. Cuprous chloride (0.589 g) was divided into seven equal portions: one portion was added to the reaction mixture and then a solution of 23.9 g of sec-butyl crotonate in 120 ml of dry diethyl ether was added dropwise over 3 hours, during which time the six remaining portions of cuprous chloride were added at 30-minute intervals. After stirring the mixture at 5° C. for 15 minutes and then at room temperature for 1 hour, the reaction mixture was gradually poured into an ice-cooled mixture of 150 g of ice, 50 ml of concentrated hydrochloric acid and 60 ml of diethyl ether with vigorous stirring. The organic layer was separated from the reaction mixture obtained and the aqueous layer was extracted with diethyl ether. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, and then concentrated. The residue was purified by distillation under reduced pressure to give 27.8 g of the title compound having the following physical characteristics:

1. temperatureto maintain
2. temperaturea constant reflux of the reaction mixture
3. temperaturewas heated
4. temperatureto reflux for a further 15 minutes
5. additionone portion was added to the reaction mixture
6. additionwere added at 30-minute intervals
7. waitat room temperature for 1 hour
8. temperaturecooled
9. customThe organic layer was separated from the reaction mixture
10. customobtained
11. extractionthe aqueous layer was extracted with diethyl ether
12. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
13. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulphate
14. concentrationconcentrated
15. distillationThe residue was purified by distillation under reduced pressure

ORD-Eintrag

ord-4304f494f6a2468e835369f2be091dcb

Quelldatensatz

uspto-grants-1981_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04294849