Ethanol → HCID 21071823, compound

Participants

Reaction Conditions

Reaction Steps

A three liter three-necked round bottom flask, equipped with heating mantle, stirrer, nitrogen inlet, and condensor, was charged with 900 mL of ethanol, 150 mL of water, 180 g (1.00 mole) of D-glucose, 119 g (1.00 mole) of tin powder (−100 mesh), and 121 g (1.00 mole) of allyl bromide. The mixture was stirred and slowly heated at 60° C. The gray suspension was stirred at this temperature for 24 hours, in which time the reaction mixture turned a light yellow color. Heat was removed and the mixture was allowed to cool to room temperature. The reaction was neutralized to pH=7 by adding approximately 200 ml of 5M NaOH aqueous solution. The suspension was filtered to remove solids, and the yellow solution was decolorized with multiple treatments of activated carbon. The activated carbon was removed by filtration, and the solvent was removed by rotary evaporation to isolate a white syrup. Typical yield was 200 g with a threo-erythro ratio of 6:1, based on GC-MS. The 1-allyl sorbitol syrup was used without further purification.

Provenance & Evidence