Aluminum(III) Chloride → HCID 23293641, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-fluorophenyl)-3-methylbutyryl chloride (19.0 g, 0.0815 mol) in dichloromethane (100 ml) was added dropwise over 2.5 h to a stirring mixture of aluminum chloride (13.57 g, 0.102 mol, Aldrich) in dichloromethane (200 ml) while protected from moisture by a nitrogen atmosphere. After stirring 18 h at 25° C., the reaction solution was poured over ice (400 g) and the resulting solution was extracted with dichloromethane (2×200 ml). The dichloromethane layers were combined, washed with deionized water (50 ml), and concentrated by spin evaporation in vacuo. The residue was dissolved in ethyl acetate and washed through a pad of silica gel. The pad was washed with additional ethyl acetate. Removal of the volatiles from the combined washes by spin evaporation in vacuo gave 15.2 g (99%) of 6-fluoro-3,3-dimethyl-1-indanone as a light yellow oil which crystallized on standing, m.p., 57-62° C.:

Provenance & Evidence