Allyl bromide → 3-Allyloxycarbonyl-5-nitrobenzoic acid

Participants

Reaction Steps

Starting material (1(c)) was prepared as described in Example 1. Starting material 7(d) was prepared as follows. A mixture of potassium carbonate (17.00 g), 5-nitro-isophthalic acid (52.00 g), allyl bromide and dimethylacetamide (400 ml) was stirred at 90° for 4 h. Dimethylacetamide was evaporated away under reduced pressure and the residue was dissolved in ethyl acetate, washed with water (2×300 ml) and then extracted with aqueous saturated sodium bicarbonate solution (3×300 ml). The extracts were combined, acidified to pH 4 with concentrated hydrochloric acid and reextracted with ethyl acetate (2×300 ml). The extracts were combined, washed with water (300 ml), dried over magnesium sulphate and evaporated under reduced pressure to give 5-nitro-isophthalic acid 3-allyl ester (7(a)) as a cream solid (39.48 g).

Provenance & Evidence