Potassium Hydroxide → Bis(2-ethynylphenyl) pentanedioate

Participants

Reaction Steps

A 500-ml., three-necked, round-bottomed flask equipped with a thermometer and mechanical stirrer was charged with a solution of potassium hydroxide, 39 g. (0.700 mole) in 360 ml. of water and then 11.7 g. (0.100 mole) of o-hydroxyphenyl acetylene (I) was added. The resulting mixture was stirred vigorously and cooled with an ice-water bath to a temperature of 10°, and then 34 g. (0.200 mole) of glutaryl chloride was added over a period of about 5 minutes. The temperature of the reaction mixture rose to 34° and subsided. After stirring at 10° C. for an additional 1.5 hours, the reaction mixture was extracted with four 200 ml-portions of ether. The combined ethereal extracts were washed with 200 ml. of 10% potassium hydroxide solution and two 200 ml-portions of water, dried, and concentrated in vacuo to give 13.0 g. (78% yield) of the desired product.

Provenance & Evidence