Sodium perbenzoate

Sodium i-nitro-2-naphtholate, 13, 78 Sodium perbenzoate, 13, 86 Sodium succinate, 12, 72 Sodium sulfide, 12, 68, 76 16, 72 Soxhlet extractor, 16, 69 17, 74 Stannic chloride, 18,1 Stannous chloride, 17, 10, 11 Steam distillation, rapid, 17, 20 Stilbene, 17, 90... 

By the action of sodium ethoxide in absolute ether, it is decomposed into sodium perbenzoate and benzoic ester —... 

Sulfonyl carbanions of primary and secondary sulfones may also be converted to the ketones by reaction with either BTSP (185) (method 1) or chlorodimethoxyborane (186) (method 2). With the latter reagent, subsequent treatment of the intermediate boric ester with sodium perbenzoate affords the ketone (Scheme 74). The use of the sodium salt of the peroxycarboxylic acid avoids side reactions and hence increases the yield of the ketone. 

Use as a base. For the conversion of dibenzoyl peroxide into sodium perbenzoate, sodium methoxide is preferred to sodium ethoxide because it is more soluble in methanol and does not precipitate provided that the temperature does not fall below... 

Sodium methylate is preferred to sodium ethylate because it is more soluble in the excess of alcohol, and does not precipitate provided the solution is not cooled below — 5°. If sodium ethylate is used the sodium perbenzoate precipitates immediately as a white powder when the sodium ethylate is added to the chloroform solution of benzoyl peroxide. In the case of sodium methylate the solution turns milky, but no precipitate appears. 

The above procedure is a considerable improvement, especially in ease of manipulation and time required, over that given in Coll. Vol. I, 422. It has been found that chloroform is more suitable than ether or toluene as a solvent for the benzoyl peroxide. A further improvement in the present method consists in the substitution of sodium methylate for sodiiun ethylate. The sodium methylate is much more soluble in the excess of alcohol, and the sodium perbenzoate remains in solution, thus assuring a quantitative conversion. The directions given in Coll. Vol. I, 422 contain two errors The amount of sodium specified (23 g.) is twice the correct amount, and the percentage yield stated as 90 is actually only 65. 

Sodium perbenzoate is reduced by hydrogen peroxide. Radioactive tracer studies (68) suggest the following transition state with compatible reaction termini. 

---