Toluene → HCID 54480429, compound

Participants

Reaction Conditions

Reaction Steps

2,4-Hexadiyn-1,6-diol (66.1 g, 0.6 mole), triethylamine (70 g) and (THF) (400 ml) were charged into a 1-liter flask which was equipped with a mechanical stirrer, thermometer, gas inlet, and a dry ice condenser. The solution was brought to 50° C. under a blanket of nitrogen. A solution of cinnamoyl chloride (110 g, 0.6 moles) and THF (200 ml) was added through a dropping funnel to the above solution which was vigorously stirred over a period of one hour at 45° . The resulting solution was held for 5 hours at this temperature and then heated to 55° C. and held at this temperature for an additional 20 hours to complete the reaction, after which the THF was stripped off and the remaining solid was redissolved in 500 ml of toluene. The toluene solution was washed three times with water, dried over magnesium sulfate and filtered After the toluene was removed from the filtrate, 134 g. of the colorless, crystalline 2,4-hexadiyn-1,6-diyl dicinnamate product having a m.p. of 102-104° was identified by NMR and IR analyses. One gram of the dicinnamate was spread on a filter paper and subjected to UV irradiation at 254 nm. After 30 seconds, no color change was observed; indicating that this product is unsuitable for photoimaging.

Provenance & Evidence