Anisole → Cyclobutyl(4-methoxyphenyl)methanone

Reaction equation

[Al+3].[Cl-].[Cl-].[Cl-].[CH:5]1([C:9]([OH:11])=O)[CH2:8][CH2:7][CH2:6]1.[C:12]1([O:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[N+](CC)([O-])=O>[CH:5]1([C:9]([C:15]2[CH:16]=[CH:17][C:12]([O:18][CH3:19])=[CH:13][CH:14]=2)=[O:11])[CH2:6][CH2:7][CH2:8]1

Participants

Procedure

A solution of AlCl3 (13.4 g) in nitroethane (25 ml) was added to a solution of cyclobutane carboxylic acid (10.0 g) and anisole (10.8 g) in nitroethane (75 ml) at 10° C. The mixture was stirred for 5 hours at room temperature, was than poured on ice and extracted with MTBE. The organic phase was washed with aqueous sodium hydroxide, water and brine, dried (MgSO4) and concentrated in vacuo. The essentially clean ketone (10.8 g) was used in the next step.