Synthesis procedures with tetrabutylammonium hydroxide

Anhydro-B-D-glucopyranose has been identified as a product from hydrothermolysis of cellulose and its degradation in aqueous solution at 200-240°C examined.A mild procedure for the synthesis of 1,6-anhydrohexopyranoses involves treatment of the pentabromophenyl g-glycosides (obtained in two steps from the B-peracetates) with tetrabutylammonium hydroxide at 20°C, followed by... 

A recent literature report described a green procedure for the condensation of arylacetonitriles with cyclic ketones using phase-transfer catalysis. This process was applied to the synthesis of venlafaxine, which was realized in overall 30% yield in two steps from commercially available 14. The condensation step was run in aqueous sodium hydroxide in the presence of tetrabutylammonium sulfate, to provide quantitative yield of intermediate 15. Hydrogenation in a formalin-methanol mixture provided the final product venlafaxine (1) in 30% overall yield. This protocol did not necessitate intermediate purification steps, making it attractive from the commercial standpoint. 

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