Methanol → Methyl neodecanoate

Temperature

55 °C

neo-Decanoic acid (1,376 g, 8.0 mol) and methanol (1,280 g, 40 mol) were placed in a 5-liter four-neck round-bottomed flask equipped with a mechanical stirrer, a condenser and a thermometer. To the mixture at ambient temperature was added conc sulfuric acid (548 g, 5.6 mol) in a dropping funnel for 15 min, raising the pot temp to 55° C. at the end of the addition. The resulting mixture was kept overnight (20-24 h) under reflux with vigorous stirring and then cooled to ambient temperature. The aqueous phase separated, and the remaining organic layer was washed with water until the pH of the last washing was >4. One gram of the organic phase was withdrawn and titrated with 1.0 N NaOH. The calculated amount of NaOH was added to remove the unreacted neo-decanoic acid present in the crude ester. Then the ester was washed with water (88 mL×3) followed by brine (NaCl-saturated, 500 mL). About 100 mL methanol was added into the crude ester and then the resulting mixture was distilled to obtain methyl neodecanoate (749 g, 4.03 mol) at 175-205° C. at atmospheric pressure. The purity of the ester was >99%, and the yield 50% yield.

1. customequipped with a mechanical stirrer, a condenser
2. additionat the end of the addition
3. temperature(20-24 h) under reflux
4. temperaturecooled to ambient temperature
5. customThe aqueous phase separated
6. washthe remaining organic layer was washed with water until the pH of the
7. washlast washing
8. customOne gram of the organic phase was withdrawn
9. additionThe calculated amount of NaOH was added
10. customto remove the unreacted neo-decanoic acid present in the crude ester
11. washThen the ester was washed with water (88 mL×3)
12. additionAbout 100 mL methanol was added into the crude ester
13. distillationthe resulting mixture was distilled

ORD record

ord-3cd993b3c93345cd8e0056ac3e6ab0ba

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05936129