Ethanol → HCID 21071824, compound

HRID 1364983Notes

Reaction equation

HRID 1364983 reaction equation
C(O)C.[O:4]=[CH:5][C@@H:6]([C@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7].[Sn].[CH2:15](Br)[CH:16]=[CH2:17]>O>[CH2:17]([CH:12]([OH:13])[C@@H:10]([C@H:8]([C@@H:6]([CH2:5][OH:4])[OH:7])[OH:9])[OH:11])[CH:16]=[CH2:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 7841Allyl bromideHCID 644160aldehydo-D-XyloseHCID 5352426Tin atom

Product 1

HCID 21071824HCID 21071824, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A five liter three-necked round bottom flask, equipped with heating mantle, stirrer, nitrogen inlet, and condenser, was charged with 1.8 liters of ethanol, 0.3 liters of water, 300 g (2.00 mole) of D-xylose, 242 g (2.04 mole) of tin powder (−325 mesh), and 242 g (2.00 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 three 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 400 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 320 g. 1H NMR (300 MHz, D2O, ppm): 2.33-2.39 (m, 2H), 3.55-3.89 (m, 6H), 5.14-5.23 (m, 2H), 5.89 (m, 1H). The syrup was used without further purification.

Workup

  1. customA five liter three-necked round bottom flask, equipped
  2. temperaturewith heating mantle, stirrer, nitrogen inlet, and condenser
  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 three days, in which time the reaction mixture
  7. temperatureHeat
  8. customwas removed
  9. additionby adding approximately 400 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

Sources & evidence

ORD record
ord-0d7d867bc29d4c5c94b1050831021c63
Source dataset
uspto-grants-2011_02
Patent number
US07888454B2

Reaction notes

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