- A synthetic method of Vinyl laurate
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Please provide with a thermometer, a reflux condenser, and a gas inlet tube through which a stream of nitrogen is passed are placed 206 g (2.4 moles) of freshly distilled vinyl acetate and 80 g (0.4 mole) of acid in a 500 ml round-bottomed three-necked flask. The lauric acid is dissolved by warming, and 1.6 g of mercuric acetate is added. The mixture is shaken by hand for about 30 minutes, and 0.15 ml of 100% sulfuric acid is added dropwise. The solution is heated under reflux for 3 hours, then 0.83 g of sodium acetate trihydrate is added to neutralize the sulfuric acid. The excess vinyl acetate is recovered by distillation at atmospheric pressure (vapor temperature about 70–80°C) until the pot temperature reaches 125°C. The distillation is completed at 10 mm or lower, and, after the collection of a small quantity of low-boiling material, fairly pure vinyl laurate is obtained as a colorless liquid, b.p. 142–143°C/10 mm (138–139°C/8 mm; 124–126°C/3 mm). The yield is 50–57 g (55–63%). Redistillation yields 48–53 g (53–59%) of pure vinyl laurate (CAS NO. ), b.p. 142–142.5°C/10 mm.
The synthetic route of Vinyl laurate is as follows:
The procedure described is substantially that of Toussaint and MacDowell, with minor modifications. Vinyl esters of long-chain aliphatic acids have also been prepared by the reaction of acetylene with the appropriate acids,5,6,7,8 but this reaction is not so convenient for small-scale laboratory preparations.
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