3-(4-[1,3]Dioxolan-2-yl-3,5-dimethylphenyl)-2,2-dimethylpropionic acid methyl ester → Methyl 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropanoate
Reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:20])([CH3:19])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]2OCC[O:14]2)=[C:8]([CH3:18])[CH:7]=1>CC(C)=O.O>[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:19])([CH3:20])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]=[O:14])=[C:8]([CH3:18])[CH:7]=1Participants
4
Procedure
To a stirred solution of 3-(4-[1,3]dioxolan-2-yl-3,5-dimethylphenyl)-2,2-dimethylpropionic acid methyl ester (1.7 g, 5.8 mmol) in acetone (20 mL) and water (0.3 mL) was added Amberlyst-15 (233 mg). The suspension was stirred at ambient temperature overnight and the suspension was filtered and washed with acetone. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (5:1) to give 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropionic acid methyl ester as a pale-yellow oil.