Hydrochloric Acid → HCID 22904134, compound

Participants

Reaction Steps

Dimethyl sulfate (0.54 g, 4.3 mmol) was added dropwise into a mixture of [2-chloro-6-(5-chloro-naphthalen-2-ylmethyl)-4-formyl-5-hydroxy-3-methyl-phenoxy]-acetic acid methyl ester (0.76 g, 2.05 mmol), potassium carbonate (0.65 g, 4.8 mmol) and acetone (75 mL). The mixture was refluxed for 2 hours, poured into water, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation gave a yellow oil, which was dissolved in MeOH (15 mL), THF (15 mL) and treated with KOH (10%, 3.1 mL). After stirring for 4 hours the mixture was poured into water, acidified with HCl (2N), and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from hexane/EtOAc, gave an off-white solid (0.34 g, 43% yield, m.p. 191°-192° C.).

Provenance & Evidence