4-(3-Chloropropoxy)-3-methoxyacetophenone → 1-(4-(3-Chloropropoxy)-3-hydroxyphenyl]ethanone

Participants

Reaction Steps

A mixture of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (10.0 g, 0.0412 mol) and concentrated H2SO4 (50 ml) was stirred at 65° for 23 hours. The cooled reaction was poured into 250 g of ice and was stirred vigorously for 10 minutes. The aqueous mixture was extracted with dichloromethane (CH2Cl2) and the resultant dichloromethane extract was washed well with 5% sodium hydroxide. The basic phases were combined and washed with dichloromethane. The aqueous mixture was cooled in an ice bath and concentrated hydrochloric acid was added until a precipitate formed. The product was isolated by filtration and dried to yield 3.1 of a light brown solid. This was combined with an additional sample (5.0 g total) and two consecutive recrystallizations from toluene provided 3.4 g (22%) of 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone as a beige solid, m.p.=101°-103° C.

Provenance & Evidence