Sodium Bicarbonate → 4-(Benzyloxy)cyclohexanone

Reaction equation

C1O[C:4]2([CH2:9][CH2:8][CH:7]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:6][CH2:5]2)[O:3]C1.C([O-])(O)=O.[Na+]>CO.Cl>[CH2:11]([O:10][CH:7]1[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Procedure

A solution of 4-benzyloxy cyclohexanone ethylene ketal 40 (5.0 g, 20.1 mmol) in methanol (20 mL) and 1N HCl (0.5 mL) was stirred overnight at 25° C. (Step 37). The mixture was neutralized by addition of 1N NaHCO3 (0.5 mL), solvent removed by roto-evaporation, and the residue chromatographed on silica gel using 15:85 ethyl acetate /hexane. Yield of the ketone 41 was 2.7 g ##STR8## (67%); Rf=0.35; 1H NMR (CDCl3) δ2.3 (m, 8H, ring-CH2), 3.6 (m, 1H, CH--O ), 4.6 (s, 2H, CH2 --O).