p-Toluenesulfonic acid → HCID 54118752, compound

Participants

Reaction Steps

Cinnamylthiopropionic acid, m.p. 87° C., was prepared from cinnamyl bromide and mercaptopropionic acid and oxidised by the method described in Example 23(a) to cinnamylsulphonylpropionic acid, m.p. 160° C. This acid was reduced by addition to a stirred suspension of lithium aluminium hydride (2 equivalents) in tetrahydrofuran at -20° to -25° C. and the product formed isolated by ethyl acetate extraction to give cinnamyl 3-hydroxypropyl sulphone, m.p. 86° C. A solution of cinnamyl 3-hydroxylpropyl sulphone, para-toluene sulphonic acid (catalytic) and dihydropyran (2 equivalents) in dichloromethane was allowed to stand at room temperature for 24 hours, evaporated, and recrystallised from diethyl ether to give the title compound, m.p. about 45° C.

Provenance & Evidence