Solketal → Isopropylideneglycerol

HRID 898086Notes

Reaction equation

[OH-].[Na+].CC1(C)[O:8][CH:7]([CH2:9][OH:10])[CH2:6][O:5]1.[CH2:12](OCC=C)[CH:13]1O[CH2:14]1>CCOCC>[C:13](=[C:9]([CH:7]([CH2:6][OH:5])[OH:8])[OH:10])([CH3:14])[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A catalytic quantity of NaOH (MW 40.00; 0.6 mol-24 g) is added to 1.2-isopropylidene-rac-glycerol (MW 132.16; 16 mol-2115 g), which is rendered a solution by stirring and heating to 80° C. At 80° C., allyl glycidyl ether (MW 114.14; 6 mol-685 g) is added dropwise over a period of 2 hours, and the reaction mixture stirred for another 2 hours at 80° C. By this point in time the epoxide (Rf in ether=0.8) has reacted completely to form the G3 constituent (Rf in ether=0.6) The excess isopropylidene-rac-glycerol has an Rf of 0.65 in ether and is removed from the reaction mixture at 75° C./10 mbar. The residue has 1 l diisopropyl ether added to it and is extracted twice with 1 l NaCl (1% solution in H2O) in each case. The organic phase is rotated in an evaporator and distilled (Kpi10-1 mbar 125° C.).

Workup

stirringthe reaction mixture stirred for another 2 hours at 80° C

Sources & evidence

ORD record: ord-7bcb54a47354404383ce3f94e81486d4
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351428B2

Reaction notes

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