Methanol → Heptanoic acid, 2-methyl-6-oxo-, methyl ester

Temperature

65 °C

43 g of a racemate of 2-methyl-6-oxoheptanoic acid (purity 99.65%, 0.27mmol) was dissolved in214.25 g of methanol, then, 2.14 g of concentrated sulfuric acid was added and mixed. Next, the mixture was heated up to 65° C., then, reacted for 5 hours at the same temperature. After completion of the reaction, the reaction mixture was cooled down to room temperature. Next, the reaction mixture was concentrated under reduced pressure until reaching about one-forth of the original weight, then, 30 g of water was added. Further, 128.55 g of methyl t-butyl ether (MTBE) was added, then, 55.06 g of a 5% sodium hydrogen carbonate aqueous solution was dropped at room temperature while stirring. The resultant mixture was stirred sufficiently at room temperature, then, liquid-partitioned, and the aqueous layer was further partitioned with 64.27 g of MTBE. The resultant organic layer was combined, and concentrated under reduced pressure, to obtain 45.4 g (content 94.3%, yield 92%) of a coarse product of a racemate of 2-methyl-6-oxoheptanoic acid methyl ester as colorless oil. The resultant coarse product was used as it is in the subsequent reaction (the resultant coarse product may be, if necessary, distilled (boiling point 107° C./1333 Pa), then, used in the next reaction).

1. additionmixed
2. customreacted for 5 hours at the same temperature
3. customAfter completion of the reaction
4. temperaturethe reaction mixture was cooled down to room temperature
5. concentrationNext, the reaction mixture was concentrated under reduced pressure
6. addition30 g of water was added
7. additionFurther, 128.55 g of methyl t-butyl ether (MTBE) was added
8. addition55.06 g of a 5% sodium hydrogen carbonate aqueous solution was dropped at room temperature
9. stirringThe resultant mixture was stirred sufficiently at room temperature
10. customliquid-partitioned
11. customthe aqueous layer was further partitioned with 64.27 g of MTBE
12. concentrationconcentrated under reduced pressure

ORD record

ord-4d1f6eda47cf4ea98b711dc40a05038c

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026081B2