Acetone → 6-(Hydroxymethyl)-2,3-dihydro-1H-inden-1-one

Reaction equation

[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.C(=O)([O-])[O-:13].[K+].[K+].[CH3:18][C:19]([CH3:21])=[O:20]>O>[OH:13][CH2:11][C:1]1[CH:2]=[C:21]2[C:4]([CH2:3][CH2:18][C:19]2=[O:20])=[CH:5][CH:6]=1

Participants

Procedure

A solution of Example 28 (8.0 g, 38.7 mmol) and p-toluenesulfonic acid (7.4 g, 38.7 mmol) in a mixture of water (20 mL) and acetone (85 mL) was heated to reflux for about 1 hour. The mixture was concentrated under vacuum, diluted with water, and neutralized by careful addition of potassium carbonate (2.7 g, 19.4 mmol). The precipitate was collected by filtration, washed with minimal water and diethyl ether, and dried under vacuum to provide the desired product. MS (DCI-NH3): m/z 180 (M+NH4)+.