Sodium Hydroxide → HCID 15229875, compound

Participants

Reaction Steps

10.5 g (0.0245 mol) of the ethyl 2-{4-[2-(4-acetoxy-2,3,5-trimethylphenoxy)ethyl]phenoxy}isobutyrate so obtained are introduced with 500 ml of ethanol and 50 ml of 1N sodium hydroxide solution into a three-necked flask that is equipped with a stirrer and a condenser and is placed under a nitrogen atmosphere. The whole is heated under reflux for 3 hours and then concentrated to dryness. The residue is taken up in water and extracted several times with ether. The aqueous phase is acidified with 55 cm3 of 1N hydrochloric acid and then extracted several times with ether. The combined ethereal phases are washed with water, dried over sodium sulphate and concentrated to dryness. The residue is chromatographed on 1.4 liters of Amicon silica (0.035-0.070 mm) while eluting with a mixture of methylene chloride and ethyl acetate (70:30). The desired fractions are concentrated to dryness. The residue is dissolved in 20 ml of ether. The whole is diluted with petroleum ether and cooled. Crystallisation is observed. The crystals are filtered off with suction and dried at 45° C. under 133 Pa to yield 6 g of 2-{4-[2-(4-hydroxy-2,3,5-trimethylphenoxy)ethyl]phenoxy}isobutyric acid in the form of white crystals melting (K) at 69° C. Yield: 68%.

Provenance & Evidence