2-Methyl-2-(pent-4-yn-1-yl)propanedioicacid → 2-Methylhept-6-ynoic acid

A mixture of 2-methyl-2-(pent-4-ynyl)malonic acid (5.7 g) and cuprous oxide (0.22 g) in acetonitrile (150 ml) was heated to reflux, under a nitrogen atmosphere, for 4.25 hours. The solvent was removed under reduced pressure and water (50 ml) was added to the residue followed by sufficient concentrated hydrochloric acid to hydrolyse the copper salts. The resulting aqueous phase was extracted with diethyl ether and the organic extracts were washed with water and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. 2-Methylhept-6-ynoic acid (3.6 g) was obtained as a colourless oil after distillation (b.p. 150°-165°, 0.5 mm Hg).

1. temperaturewas heated
2. temperatureto reflux, under a nitrogen atmosphere, for 4.25 hours
3. customThe solvent was removed under reduced pressure and water (50 ml)
4. additionwas added to the residue
5. extractionThe resulting aqueous phase was extracted with diethyl ether
6. washthe organic extracts were washed with water and brine
7. dry with materialbefore drying over anhydrous magnesium sulphate and evaporation in vacuo

ORD record

ord-3e727cac35f640b383df5c84692b4630

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05116862