Hydrogen Peroxide → 3-Ethylbenzene-1,2-diol

Participants

Reaction Conditions

Reaction Steps

To a solution of crude 9 (ca. 80 mmol) in 2N NaOH (40 mL) cooled to 0-5° C., a solution of ca. 7% hydrogen peroxide (49 mL) was added dropwise over 30 min while maintaining the temperature at 20° C. The reaction was stirred for further 45 min then diluted with AcOEt (ca 250 mL), washed with HCl 2N (ca 50 mL). The aqueous layer was e-extracted with AcOEt and the combined organic extracts were washed with brine, and dried over sodium sulphate. The solvent was removed under reduced pressure to give a crude which was columned (cyclohexane:AcOEt 4:1) to give 6.4 g of 10 as a brown oil:

Provenance & Evidence