Hydrogen Peroxide → HCID 19006205, compound

Participants

Reaction Steps

The product from Stage (a) (45.8 g, 0.12 mol) was dissolved in dichloromethane (350 ml) and trifluoroacetic acid (60 ml) was added dropwise during 30 minutes. H2O2 (100 vol, 31 ml, 0.24 mol) was then added during 15 minutes and the solution was boiled under reflux for 4 hours. A further addition of H2O2 (5 ml) was made and boiling was continued for a further 5 hours when it was shown by TLC (SiO2, CHCl3 :CH3CO2C2H5 =1:1) that only a trace of starting material remained. The mixture was poured onto ice and the organic solution was extracted with aqueous sodium carbonate and water, dried (MgSO4) and concentrated at 0.2 mm pressure to 46 g of oil. Microanalysis for C22H36NO3Cl, % theory (found): C: 66.39 (66.2); H: 9.12 (9.5); N: 3.52 (3.2); Cl: 8.91 (8.7). M.S. m/z=397. NMR(CDCl3)=7.65 (m, 2, ArH), 8.90 (2, 1, ArH), otherwise as starting material.

Provenance & Evidence