Toluene → Methyl 16-bromohexadecanoate

Temperature

55 °C

16-Bromo-hexadecanoic acid (6.0 g) was dissolved in MeOH (35 mL), toluene (100 mL) and trimethylorthoformate (20 mL), then Amberlyst 15 from Fluka (1.4 g) was added. The mixture was stirred at 55° C. for 16 h. The mixture was evaporated to dryness and dried under vacuum for 16 h to yield 7.7 g. The residue was suspended in MeOH (ca. 50 mL) and stirred for ca ½ h. The amberlyst 15 was filtered off after stirring with DCM (30 mL) for ½ h. The filtrate was concentrated to remove the DCM, and the clear solution was cooled and more MeOH (ca 20 mL, total ca 40 mL) was added. The flask was cooled and more crystals precipitated and after stirring for 30 min, the crystals were filtered off and washed with cold MeOH. The white crystals were dried under vacuum to yield 5.61 g.

1. customThe mixture was evaporated to dryness
2. customdried under vacuum for 16 h
3. customto yield 7.7 g
4. stirringstirred for ca ½ h
5. filtrationThe amberlyst 15 was filtered off
6. stirringafter stirring with DCM (30 mL) for ½ h
7. concentrationThe filtrate was concentrated
8. customto remove the DCM
9. temperaturethe clear solution was cooled
10. additionmore MeOH (ca 20 mL, total ca 40 mL) was added
11. temperatureThe flask was cooled
12. custommore crystals precipitated
13. stirringafter stirring for 30 min
14. filtrationthe crystals were filtered off
15. washwashed with cold MeOH
16. customThe white crystals were dried under vacuum
17. customto yield 5.61 g

ORD record

ord-aab525d342c445429b87628c37e56b6d

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648041B2