Hydrochloric Acid → (p-Hydroxyphenyl)propiolonitrile

A solution of 381 mg of p-[(trimethylsilyl)ethynyl]phenol in 5 ml of hexamethylphosphoric acid triamide was treated at -5° C. in a sulphonation flask under argon gasification with 2.5 ml of a 1.75M solution of methyl lithium in diethyl ether. 15 minutes after completion of the addition the mixture, which had become a red slurry, was diluted with 5 ml of absolute tetrahydrofuran and subsequently stirred at room temperature for 3 hours. The mixture was then cooled to -30° C. and 322 μl of phenyl cyanate were added. The new brown-orange clear solution was warmed to 0° C. within 60 minutes, then poured into 50 ml of 1N hydrochloric acid and extracted three times with 50 ml of diethyl ether each time. The organic phases were washed a further three times with 50 ml of water each time (to which was added a small amount of sodium chloride solution), dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.4 bar) of the orange residue (570 mg) on silica gel with 15% ethyl acetate/petroleum ether followed by 20% ethyl acetate/petroleum ether gave 160 mg (56%) of (p-hydroxyphenyl)propiolonitrile as light yellowish crystals; m.p. 134°-137° C.

1. addition15 minutes after completion of the addition the mixture, which
2. temperatureThe mixture was then cooled to -30° C.
3. temperatureThe new brown-orange clear solution was warmed to 0° C. within 60 minutes
4. extractionextracted three times with 50 ml of diethyl ether each time
5. washThe organic phases were washed a further three times with 50 ml of water each time (to which
6. additionwas added a small amount of sodium chloride solution),
7. dry with materialdried over magnesium sulphate
8. concentrationconcentrated

ORD record

ord-2e6c0b9ed5e647d6ab1ea79696558697

Source dataset

uspto-grants-1985_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04528114