Cyclopropanecarboxylic acid 4-chloro-3-hydroxymethyl-benzylamide → Cyclopropanecarboxylic Acid 4-chloro-3-formyl-benzylamide
Reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[CH2:15][OH:16]>CC#N.O=[Mn]=O>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:11][CH2:12]2)=[O:9])=[CH:4][C:3]=1[CH:15]=[O:16]Participants
4
Procedure
MnO2 (6.29 g, 72.0 mmol) was added to a sol. of cyclopropanecarboxylic acid 4-chloro-3-hydroxymethyl-benzylamide (3.47 g, 14.0 mmol) in CH3CN (300 mL) at rt. The mixture was stirred for 3 h at rt, and MnO2 (2.52 g, 29.0 mmol) was added again. The mixture was stirred for 1 h at rt, and MnO2 (1.26 g, 14.0 mmol) was added again. The mixture was stirred for 1.5 h, and was filtered through celite. The filtrate was evaporated under reduced pressure, and the residue was dried under high vacuum to yield the crude title compound (3.13 g, 91%) that was used further without purification. LC-MS: tR=0.80 min; ES+: 279.31.