Degradation using mixed anhydride reagent

Tsuji and Konishi [29] described the preparation of the acetate of the alcohols in phosphate esters, and the diacetate of the ethylene glycol derived from the ethylene oxide in alkylether phosphates, with subse- 

The authors did not say how quantitative this is, but it is potentially an attractive approach, because all three products would be easy to determine by chemical means. 

Reagent. Place 120 g p-toluenesulphonic acid in a 300 ml round-bottomed flask. Slowly and with stirring, add 80 g acetic anhydride. Attach a reflux condenser and heat at 120°C for 30 min on an oil bath. Cool and store in a brown bottle. The reagent will keep for 1 month. 

Extract with three or four 20 ml portions of diethyl ether. 

Combine the ether extracts and wash with several portions of water until the washings are no longer acid to methyl orange. 

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Cellulose esters of halogenated acids are exceptionally difficult to prepare. This is particularly true if the halogen is in the alpha position to the carboxyl group. Chloroacetic anhydride in the presence of acid catalysts esterifies cellulose only after severe degradation. The use of pyridine is prohibited because of side reactions with the reagent. Mixed... 

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