Sodium Hydroxide → (2-Hydroxyphenyl)acetic acid

Participants

Reaction Conditions

Reaction Steps

Solid pearl sodium hydroxide (as discrete spheres) (24 g) was suspended in `SOLVESSO` 200 (100 ml) at 25° C. (2-Chlorophenyl)acetic acid (17.0 g) was added to this in one portion and the mixture was stirred for 20 minutes at room temperature after which time copper sulphate pentahydrate (1.0 g) was added. The reaction mixture was then heated and stirred at 180° C. After 15 hours gas/liquid chromatography indicated that all the (2-chlorophenyl)acetic acid had been consumed. The reaction mixture was cooled to room temperature and during this process it thickened. (The pearl sodium hydroxide was still in discrete spheres). The reaction mixture was filtered and the residue washed twice with hexane. After briefly air drying the residue, it was dissolved in water. The water solution was filtered to remove some brown solid before being washed with ethyl acetate. Charcoal was then added to the water solution and the resulting mixture was filtered through `Hyflo` (`Hyflo` is a Trade Name of Trade Mark). The filtrate was acidified to pH 3.5 and a few oily specs were formed. These were filtered off. The resulting filtrate was extracted with ethyl acetate. The extracts were combined, dried and evaporated to give a crude product (10.5 g). The crude product was recrystallised from water and then recrystallised from acetic acid to give 2.7 g of (2-hydroxyphenyl)acetic acid as a crystalline solid (melting point 141.4°-142° C.) (theoretical m.pt. 147°-149° C.).

Provenance & Evidence