Acetic Acid → HCID 178502111, compound

Participants

Reaction Steps

5.835 g of methyl carbamate, 0.275 g of p-toluenesulfonic acid monohydrate and 10.000 g of 2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid were added to 16 mL of acetic acid to be suspended. After being dissolved by heating, 80 mL of chlorobenzene was added thereto and then the solution was refluxed with vigorous stirring. A remaining solution was removed appropriately while the internal temperature of the reaction solution was maintained from 106 to 110 deg. C. under a slightly reduced pressure, followed by adding chlorobenzene, the volume of which was equal to the volume of the removed solution. Two hours later, dissipation of almost all the raw materials was confirmed by HPLC measurement. At this point, the area ratio of Z form to E form was 93:7. After removing about 50 mL of the solvent under a reduced pressure, followed by adding 20 mL of acetic acid, and then the resultant was stirred for 1 hour at 80 deg. C. The precipitate which was obtained by cooling the solution gradually to room temperature and stirring over-night, was filtered and then the filtrate was washed with acetic acid. After being washed with acetone, dried for 6 hours from 40 to 50 deg. C. under a reduced pressure, 9.505 g of the objective compound was obtained (72.2% yield, Z:E=99.5:0.5).

Provenance & Evidence