Water → 2-Methoxycarbonyl-heptadecanedioic acid 1-methyl ester

Temperature

50 °C

Sodium (1.11 g, 48.2 mmol) was dissolved in dry methanol (30 ml) and heated to 50° C. Dimethyl malonate (5.87 ml, 51.4 mmol) was added over 15 min. The mixture was heated to reflux and a suspension of 15-bromopentadecanoic acid (5 g, 15.6 mmol) in dry methanol (50 ml) was added over 45 min. The resulting mixture was refluxed for another 30 min. After cooling to RT, water was added and the mixture was concentrated. Water was added to the residue an made alkaline with 1 N NaOH and extracted with ether (1×50 ml). The aqueous layer was acidified with 1N HCl and extracted with ether (3×30 ml). The combined organic layers was dried (Na2SO4) and concentrated to give the title compound in 98% (5.7 g) yield.

1. temperatureThe mixture was heated
2. temperatureto reflux
3. additionwas added over 45 min
4. temperatureThe resulting mixture was refluxed for another 30 min
5. temperatureAfter cooling to RT
6. concentrationthe mixture was concentrated
7. additionWater was added to the residue an made alkaline with 1 N NaOH
8. extractionextracted with ether (1×50 ml)
9. extractionextracted with ether (3×30 ml)
10. dry with materialThe combined organic layers was dried (Na2SO4)
11. concentrationconcentrated

ORD record

ord-08f77dbf8bba495795483173f099a588

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476228B2