Hydrogen Peroxide → HCID 86692736, compound

Participants

Reaction Steps

The product of Step B (10 g, 21.91 mmol) was dissolved in toluene (50 mL) and 2,2-dimethylpropane-1,3-diol (2.51 g, 24.11 mmol) and catalytic TsOH were added. The solution was refluxed for 3 h with a Dean-Stark trap in place, then cooled to rt, concentrated and flushed with THF. The product was dissolved in THF (70 mL), and cooled in an ice/acetone bath to 0° C. Hydrogen peroxide (5.76 mL, 35%, 65.7 mmol), followed by LiOH (1.05 g, 43.8 mmol in 8 mL water) were added and the mixture was allowed to warm and age at rt. The reaction mixture was acidified and heated to 60° C. for 1 h, then re-cooled to rt, and extracted with MTBE. The organic layer was collected, dried (Na2SO4), filtered and concentrated. The crude product was re-dissolved in MTBE and N-cyclohexylcyclohexanamine was added. The resulting slurry was aged for 1 h and filtered. The wet cake was washed with MTBE and the solid was dried under a vacuum/N2 sweep to afford the title compound.

Provenance & Evidence