Sodium Bicarbonate → 4-(Benzyloxy)cyclohexanone

HRID 2393936Notes

Reaction equation

HRID 2393936 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

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 109873694-(Benzyloxy)cyclohexanone

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

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 (67%); Rf=0.35; 1H NMR (CDCl3) δ 2.3 (m, 8H, ring--CH2) 3.6 (m, 1H, CH--O), 4.6 (s, 2H, CH2 --O).

Workup

  1. customremoved by roto-evaporation
  2. customthe residue chromatographed on silica gel using 15:85 ethyl acetate/hexane

Sources & evidence

ORD record
ord-0b1d0254b1914024ad1d5d9b75ec6073
Source dataset
uspto-grants-1998_09
Patent number
US05808146

Reaction notes

Loading…