Benzyl Alcohol → HCID 7918796, compound

HRID 129109Notes

Reaction equation

HRID 129109 reaction equation
C(Cl)(=O)C.[CH2:5]([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[O:13]=[CH:14][C@@H:15]([C@H:17]([C@@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[OH:18])O>>[CH:9]1[CH:10]=[CH:11][C:6]([CH2:5][O:12][C@H:23]2[O:24][C@H:15]([CH2:14][OH:13])[C@@H:17]([OH:18])[C@H:19]([OH:20])[C@H:21]2[OH:22])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 6367Acetyl chlorideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 7918796HCID 7918796, compound

Conditions

Temperature
80 °C

Procedure

Acetyl chloride, 80 mL, was added carefully to 1.75 L benzyl alcohol. This was followed by the addition of 180 g glucose. The mixture was heated, with stirring, at 80° C. overnight; then cooled, and poured into a plastic bucket. The product was precipitated as an oil by the addition of ether (3 L) and hexane (15 L). The supernatant liquid was decanted, and the residual oil washed with ether-hexane 1:1 (10 L), then ether. This afforded benzyl-alpha-D-glucopyranoside as a semisolid which was filtered, crushed, and washed with ether, then hexane to afford 237.3 g (0.88 mole; 88%) white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperaturethen cooled
  3. additionpoured into a plastic bucket
  4. customThe product was precipitated as an oil by the addition of ether (3 L) and hexane (15 L)
  5. customThe supernatant liquid was decanted
  6. washthe residual oil washed with ether-hexane 1:1 (10 L)
  7. filtrationThis afforded benzyl-alpha-D-glucopyranoside as a semisolid which was filtered
  8. customcrushed
  9. washwashed with ether
  10. customhexane to afford 237.3 g (0.88 mole; 88%) white solid

Sources & evidence

ORD record
ord-52ebce87a23d4269b4d59936a1f53b20
Source dataset
uspto-grants-1995_11
Patent number
US05466809

Reaction notes

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