Hydroquinone → 2-Methylacrylic acid 6-(4-benzothiazol-2-yl-2,6-dimethoxyphenoxy)hexyl ester

Participants

Reaction Steps

A solution of 6-(4-benzothiazol-2-yl-2,6-dimethoxy-phenoxy)hexan-1-ol (1.10 g, 0.0038 mol), methacrylic acid (1.30 g, 0.015 mol) of p-toluenesulfonic acid (0.10 g, 0.0005 mol), hydroquinone (0.10 g, 0.0009 mol) and toluene (50 cm3) was heated under reflux for 48 hours in a Dean and Stark apparatus to remove water continuously and then allowed to cool. The solvent was removed under reduced pressure and the residue dissolved into diethyl ether (100 cm3). The resultant solution was washed with water (20 cm3), dried (Na2SO4), filtered and then evaporated down under slightly reduced pressure. The residue was recrystallised from methanol to yield 1.16 g (67.1%) of the desired product. A small amount of 2,6-di-tert-butyl-4-methylphenol was added to act as an inhibitor to prevent spontaneous polymerisation.

Provenance & Evidence