Benzene → HCID 13151225, compound

A solution of 0.3 ml of thionyl chloride in 2 ml of benzene was added dropwise to a mixture of 0.3 g of triiodoacrylic acid, 0.3 ml of pyridine and 3 ml of benzene. The mixture was then stirred at room temperature for 45 minutes, after which the solvent was distilled off under reduced pressure. 5 ml of benzene and 0.3 ml of pyridine were added to the resulting residue, and then 0.3 g of phenol was added, with ice-cooling, after which the mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was poured into an ice-cooled dilute solution of hydrochloric acid and then extracted with diethyl ether. The extract was washed, in turn, with a saturated aqueous solution of sodium bicarbonate, water and then a saturated aqueous solution of sodium chloride. The resulting solution was dried over anhydrous sodium sulphate and then the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography through silica gel eluted with a 100:12 by volume mixture of hexane and ethyl acetate, to give 0.18 g of the title compound, melting at 83°-84.5° C.

1. distillationafter which the solvent was distilled off under reduced pressure
2. addition5 ml of benzene and 0.3 ml of pyridine were added to the resulting residue
3. addition0.3 g of phenol was added, with ice-
4. temperaturecooling
5. stirringafter which the mixture was stirred at room temperature for 2 hours
6. additionAt the end of this time, the reaction mixture was poured into an ice-
7. temperaturecooled dilute solution of hydrochloric acid
8. extractionextracted with diethyl ether
9. washThe extract was washed, in turn, with a saturated aqueous solution of sodium bicarbonate, water
10. dry with materialThe resulting solution was dried over anhydrous sodium sulphate
11. distillationthe solvent was distilled off under reduced pressure
12. customThe resulting residue was purified by column chromatography through silica gel
13. washeluted with a 100:12 by volume mixture of hexane and ethyl acetate

ORD record

ord-7e05995589f9473ead3777f209c60b46

Source dataset

uspto-grants-1983_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04421766