Glycidol → 3-Octadecylsulfanylpropane-1,2-diol

Reaction equation

[CH2:1]([SH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:20]1[O:22][CH:21]1[CH2:23][OH:24]>>[CH2:1]([S:19][CH2:20][CH:21]([OH:22])[CH2:23][OH:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Reactant 2

HCID 11164Glycidol2×

HCID 179051-Octadecanethiol2×

Product 1

HCID 2459623-Octadecylsulfanylpropane-1,2-diol

Procedure

The octadecyl mercaptan is then condensed with 4 moles glycidol per mole octadecyl mercaptan, first introducing a first molar equivalent of glycidol to obtain 3-octadecylthio-propane-1,2 diol at 80° C, the rest of the glycidol being introduced at 155° C in the course of 2 hours 20 minutes.

Sources & evidence

ORD record: ord-cf331a15f2b34f0bad518a6f66299405
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03984480

Reaction notes

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