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Propargyl bromide (22 g, 0.15 mol) was dissolved in 140 ml of n-hexane. This solution, 2-phenyl-3-butyne-2-ol (14.6 g, 0.1 mol), NaOH (60 g, 1.5 mol) and a catalytic amount of tetrabutyl ammonium hydrogen sulfate/water (120 ml) were mixed, reacted for 24 hours at an ambient temperature and refluxed for 30 minutes. After completion of the reaction, the mixture was cooled to an ambient temperature and water (100 ml) was added. The organic phase was extracted with 30 ml of n-hexane, three times. The extracted organic solvent was dried with anhydrous magnesium sulfate, filtered and evaporated to separate. b.p.: 61° C./0.5 mmHg; yield: 65%; MS: m/e 184 (parent), 129 (base).

1. customreacted for 24 hours at an ambient temperature
2. temperaturerefluxed for 30 minutes
3. customAfter completion of the reaction
4. extractionThe organic phase was extracted with 30 ml of n-hexane, three times
5. dry with materialThe extracted organic solvent was dried with anhydrous magnesium sulfate
6. filtrationfiltered
7. customevaporated
8. customto separate