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

HRID 848677Notes

Reaction equation

HRID 848677 reaction equation
[OH-].[Na+].[CH:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH2:11][O:12][C@@H:13]2[O:18][C@H:17]([CH2:19][OH:20])[C@@H:16]([OH:21])[C@H:15]([OH:22])[C@H:14]2[OH:23])=[CH:5][CH:4]=1.C1(O)C=CC=CC=1.C1OC1>CCCCOCCOCCO>[CH:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[CH2:11][O:12][C@@H:13]2[O:18][C@H:17]([CH2:19][OH:20])[C@@H:16]([OH:21])[C@H:15]([OH:22])[C@H:14]2[OH:23])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 14798Sodium HydroxideHCID 131712515HCID 131712515, compound3×

Product 1

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

Reagents, catalysts & solvents 1

HCID 8177Diethylene Glycol Monobutyl EtherSolvent

Procedure

After having added 2.1 parts of sodium hydroxide, 393.5 parts of the rosin-phenol compound described under (a) are oxethylated at 140° to 150° C. in accordance with Example 17(b). The resulting slightly viscous rosin-phenol addition product is olive green and contains 12 mols of ethylene oxide. The cloud point in butyl diglycol is found at 50.5° C.

Workup

  1. customare oxethylated at 140° to 150° C. in accordance with Example 17(b)
  2. customis found at 50.5° C.

Sources & evidence

ORD record
ord-7364f537e24a4c36a1bbca5cc9983fd1
Source dataset
uspto-grants-1981_10
Patent number
US04297270

Reaction notes

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