Sodium Hydroxide → [[8-Acetyl-7-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-naphthalenyl]oxy]acetic acid

Participants

Reaction Steps

A mixture of 1.2 g of [[8-acetyl-7-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-naphthalenyl]oxy]acetic acid methyl ester and 21 ml of 1N sodium hydroxide in 42 ml of methanol was stirred at reflux for 1 hour. The methanol was removed in vacuo and the aqueous solution was washed with ethyl acetate. The aqueous layer was acidified with 3N hydrochloric acid to pH 3 and the oil was extracted with chloroform. The extract was dried (magnesium sulfate) and concentrated to give an oil which was triturated with ether-cyclohexane and filtered to yield 0.85 g, mp 101°-104° C. (73%) of [[8-acetyl-7-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-naphthalenyl]oxy]acetic acid.

Provenance & Evidence