Ethylene Oxide → (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol

HRID 848675Notes

Reaction equation

HRID 848675 reaction equation
[OH-].[Na+].C1OC1.[CH:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[CH2:14][O:15][C@@H:16]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@H:18]([OH:25])[C@H:17]2[OH:26])=[CH:8][CH:7]=1.OCC(CO)O.CCCCOCCOCCO>>[CH:6]1[CH:7]=[CH:8][C:9](/[CH:12]=[CH:13]/[CH2:14][O:15][C@@H:16]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@H:18]([OH:25])[C@H:17]2[OH:26])=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6354Ethylene Oxide3×HCID 8177Diethylene Glycol Monobutyl EtherHCID 14798Sodium HydroxideHCID 131712514HCID 131712514, compound

Product 1

HCID 5280656(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol

Procedure

After having added 2.4 parts of sodium hydroxide, 468.5 parts of the rosin-phenol-glycerol ester described under (a) are oxalkylated in a pressure vessel, with stirring and feeding in of 616 parts of ethylene oxide at 140° to 150° C., while maintaining a pressure of from 2.5 to 3.5 bars. After the total amount of ethylene oxide has been introduced under pressure, stirring is continued for 1 hour at 140° to 150° C. The resulting viscous rosin-glycerol addition product is reddish brown and contains 14 mols of ethylene oxide. The cloud point in a 25% butyl diglycol solution is found at 60° C.

Workup

  1. customare oxalkylated in a pressure vessel
  2. temperaturewhile maintaining a pressure of from 2.5 to 3.5 bars
  3. stirringstirring
  4. customis found at 60° C.

Sources & evidence

ORD record
ord-b54dc034542a49ec859ce90ea82483b1
Source dataset
uspto-grants-1981_10
Patent number
US04297270

Reaction notes

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