Chlorination of sugars

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536120, 536119, 536 184, 536124, 536125, 536 41, C07H 100, C07H 502, C07H 106, C07H 1500

Patent

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051360314

ABSTRACT:
A process for the chlorination of sucrose or a derivative thereof, comprises reaction of the sucrose or derivative thereof with thionyl chloride and a nitrogen base at a ratio of about 1 molar equivalent (ME) of thionyl chloride and about 1 ME of base for every ME of free hydroxyl, in a non-reactive moderately polar solvent. The process is particularly suitable for the preparation of sucralose.

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Darzens, Comptes Rendues, 1911, 152, 1314, 1601; and 1912, 154, 1615, "Chimie Organique-Nouvelle methode d'etherification des alcools par les hydracides".
Gerrard, J. Chem. Soc. 1939, 99, "Studies on the Esters of Sulphurous Acid, etc. Part I"; 1940, 218 Studies on the Esters of Sulphurous, Chlorosulphinic, and Chlorosulphonic Acids. Part II; and 1944, 85, Experiments on the Interaction of Hydroxy-compounds and Phosphorus and Thionyl Halides in the Absence and in the Presence of Teriary Bases. Part I. Optically Active .beta.-Octanol, Ethyl Madelate, and Phenylmethylcarbinol.

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