Sodium Hydroxide → HCID 54249448, compound

Participants

Reaction Steps

Methyl 5-p-chlorophenylthien-2-ylacetate (5.32 g.) was stirred with a mixture of glacial acetic acid (100 ml.) and sodium acetate (4.8 g.). A solution of bromine (1 ml.) in glacial acetic acid (15 ml.) was added. The mixture was stirred for two hours and then poured into ice/waer (1 l.). After 4 days at ambient temperature the mixture was extracted with ether (4 × 200 ml.), the combined ethereal extracts were successively washed with water (3 × 200 ml.), 10% w/v aqueous sodium bicarbonate (2 × 200 ml.), and water (200 ml.), dried over anhydrous sodium sulphate, and evaporated to give a pale yellow oil. Part of this oil (1.75 g.) was refluxed with ethanol (15 ml.), water (40 ml.) and 11N-sodium hydroxide (15 ml.) for 3 hours. The mixture was added to ice/water (100 ml.) and extracted with ether (3 × 20 ml.). The aqueous layer was acidified with 2N-acetic acid and extracted with ether (3 × 20 ml.). The combined ethereal extracts were washed with water (2 × 20 ml.), dried over anhydrous sodium sulphate and evaporated in a relatively high vacuum (0.5 mm.). The residual solid was dissolved in the minimum volume of ether, and after the addition of 4 volumes of petroleum ether (b.p. 60°-80°C.), gave crystals of α-(4-bromo-5 -p-chlorophenylthien-2-yl)acetic acid, m.p. 136°-137°C.

Provenance & Evidence