1,4-Dichlorobenzene → HCID 19741711, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl α-(acetylamino)-3-(2-propenoxy)benzeneacetate from Preparation 5 above (8.0 g, 32 mmol) in 15 g of p-dichlorobenzene is heated at 350° C. for 16 hours in a sealed tube. The reaction mixture is cooled and the contents of the tube are purified by silica gel chromatography, eluting with CHCl3 to remove the p-dichlorobenzene and then with 5% MeOH-CHCl2 to remove the rearrangement products (methyl α-(acetylamino)-3-hydroxy-2-(2-propenyl) benzeneacetate, methyl α-(acetylamino)-3-hydroxy-4-(2-propenyl)benzeneacetate). The rearrangement products (a 1:1 mixture of methyl α-(acetylamino)-3-hydroxy-2-(2-propenyl)-benzeneacetate, methyl α-(acetylamino)-3-hydroxy-4-(2propenyl)benzeneacetate) are separated by silica gel chromatography (Chromatotron/EtOAc). Recrystallization from diisopropylether/THF gives the compound of methyl α-(acetylamino)-3-hydroxy-4-(2-propenyl)benzeneacetate above (2.60 g, 33%) as a white solid, mp 143°-145° C.

Provenance & Evidence