Water → HCID 18673377, compound

Participants

Reaction Steps

3.2 ml of a 300% solution of sodium methoxide in methanol were added dropwise to a solution of 611 μl of thioglycolic acid in 7 ml of methanol, under an inert atmosphere. The mixture was maintained under stirring for 30 min and then a solution of 2 g of 1-chloro-2,5-pentadecadiyne in 20 ml of methanol was added under an inert atmosphere. The mixture was maintained under stirring for 20 hours at room temperature and then the reaction medium was poured over 100 ml of acid water (98 ml of water+2 ml concentrated H2SO4) and then extracted 3 times with ethyl ether. The combined organic phases were washed 3 times with water and then with a saturated aqueous solution of NaCl before being dried (Na2SO4), filtered and concentrated under vacuum in a rotary evaporator. The oily residue obtained crystallized on cooling. 3-Thia-5,8-octadecadiynoic acid was recrystallized from diisopropyl ether and thus isolated in the form of a white solid with a yield of 26%.

Provenance & Evidence