Ethylene Glycol → 2-Hydroxyethyl naphthalene-2-carboxylate

Participants

Reaction Steps

15.6 g (252 mmol) of ethylene glycol (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.) was dissolved in 100 mL of dehydrated methylene chloride (manufactured by Kanto Chemical Co., Inc.) and 3.49 g (44.0 mmol) of pyridine was added to the solution followed by cooling down with ice water. To this solution, a solution in which 8.00 g (42.0 mmol) of 2-naphthalene carbonyl chloride (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.) was dissolved in 80 mL of methylene chloride was dripped in one hour while being stirred. Subsequent to two hour stirring, the resultant was stirred for six hours at room temperature. The reaction solution was rinsed with water and thereafter the organic phase was isolated followed by drying with magnesium sulfate (manufactured by Kanto Chemical Co., Inc.) and the solvent was distilled away. The remainder was refined by silica gel column chromatography with a solvent mixture of a methylene chloride (manufactured by JUNSEI CHEMICAL CO., LTD.) and methanol (manufactured by Kanto Chemical Co., Inc.) with a volume ratio of 97:3 serving as an eluent to obtain 6.88 g of 2-naphthoic acid 2-hydroxyethyl ester.

Provenance & Evidence