Ethanol → HCID 21071823, compound

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 to reflux—a significant exotherm and gas evolution was observed at 60° C. The gray suspension was stirred at reflux for two days, in which time the reaction mixture turned an orange/brown 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 threo-erythro ratio of 7:1, based on GC-MS. The syrup was used without further purification.

1. customA three liter three-necked round bottom flask, equipped
2. temperaturewith heating mantle, stirrer, nitrogen inlet, and condensor
3. temperatureslowly heated to reflux—a significant exotherm and gas evolution
4. customwas observed at 60° C
5. stirringThe gray suspension was stirred
6. temperatureat reflux for two days, in which time the reaction mixture
7. temperatureHeat
8. customwas removed
9. additionby adding approximately 200 ml of 5M NaOH aqueous solution
10. filtrationThe suspension was filtered
11. customto remove solids
12. customThe activated carbon was removed by filtration
13. customthe solvent was removed by rotary evaporation
14. customto isolate a white syrup
15. customThe syrup was used without further purification

ORD record

ord-368a0433f8a34513805ddf7d717275d8

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888454B2