hexadec-2-ynoic acid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of acetylenic acid 3 (37 g, 188 mmol) in 1.1 L of methanol was added 2.2 mL of concentrated sulfuric acid, and the resulting reaction mixture was heated under reflux for 16 h. Upon cooling to room temperature, the reaction mixture was concentrated to one third volume in vacuo, diluted with 1 L of 2:1 hexanes/diethyl ether, and washed with 2×50 mL of saturated aqueous sodium bicarbonate. The combined aqueous washes were further extracted with 2×150 mL of diethyl ether, treated with 50 mL of brine, combined with the previous organic extract and dried sodium sulfate. Concentration in vacuo gave a biphasic residue that was partitioned with 500 mL of hexanes and 50 mL of brine. The aqueous layer was further extracted with 2×50 mL of hexanes, the combined organic layers were dried over sodium sulfate, concentrated in vacuo, and vacuum dried to give methyl ester 4 (38.2 g, 96%) a golden-brown oil: the resulting reaction mixture was heated under reflux for 16 h the reaction mixture was concentrated to one third volume in vacuo diluted with 1 L of 2:1 hexanes/diethyl ether washed with 2×50 mL of saturated aqueous sodium bicarbonate The combined aqueous washes were further extracted with 2×150 mL of diethyl ether treated with 50 mL of brine organic extract Concentration in vacuo gave a biphasic residue that was partitioned with 500 mL of hexanes and 50 mL of brine The aqueous layer was further extracted with 2×50 mL of hexanes the combined organic layers were dried over sodium sulfate concentrated in vacuo, and vacuum dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of acetylenic acid 3 (37 g, 188 mmol) in 1.1 L of methanol was added 2.2 mL of concentrated sulfuric acid, and the resulting reaction mixture was heated under reflux for 16 h. Upon cooling to room temperature, the reaction mixture was concentrated to one third volume in vacuo, diluted with 1 L of 2:1 hexanes/diethyl ether, and washed with 2×50 mL of saturated aqueous sodium bicarbonate. The combined aqueous washes were further extracted with 2×150 mL of diethyl ether, treated with 50 mL of brine, combined with the previous organic extract and dried sodium sulfate. Concentration in vacuo gave a biphasic residue that was partitioned with 500 mL of hexanes and 50 mL of brine. The aqueous layer was further extracted with 2×50 mL of hexanes, the combined organic layers were dried over sodium sulfate, concentrated in vacuo, and vacuum dried to give methyl ester 4 (38.2 g, 96%) a golden-brown oil: the resulting reaction mixture was heated under reflux for 16 h the reaction mixture was concentrated to one third volume in vacuo diluted with 1 L of 2:1 hexanes/diethyl ether washed with 2×50 mL of saturated aqueous sodium bicarbonate The combined aqueous washes were further extracted with 2×150 mL of diethyl ether treated with 50 mL of brine organic extract Concentration in vacuo gave a biphasic residue that was partitioned with 500 mL of hexanes and 50 mL of brine The aqueous layer was further extracted with 2×50 mL of hexanes the combined organic layers were dried over sodium sulfate concentrated in vacuo, and vacuum dried