4-nitroperoxybenzoic acid

Uses

4-Nitroperoxybenzoic acid is an electrophile that transfers oxygen to alkenes.

Preparation

The reaction between Na2O2 and p-Nitrobenzoyl Chloride in THF in the  presence of small quantities of water below -5 °C furnishes the sodium salt of PNPBA. p,p′- Dinitrobenzoyl peroxide and p-nitrobenzoic acid are removed from the reaction mixture during  workup. PNPBA (purity 94-96%) is obtained in 85% yield (0.1 mol scale).

Production Methods

This peroxide can be prepared from p-nitrobenzoic acid and 90% hydrogen peroxide in methanesulfonic acid medium.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 1336, 1962 DOI: 10.1021/jo01051a050
Synthetic Communications, 18, p. 2123, 1988 DOI: 10.1080/00397918808068282

storage

At room temperature, PNPBA is stable for long periods.