Epichlorohydrin → 1,2-Epoxy-3-(12-cyclohexyldodecyloxy)propane

HRID 478106

Reaction equation

[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[O:24]1[CH:22]([CH2:20][O:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:23]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 26.5 g (99 millimole) of 12-cyclohexyldodecanol, 27.4 g (296 millimole) of epichlorohydrin, 52.6 g (658 millimole) of 50% aqueous solution of sodium hydroxide, 2.0 g of cetyltrimethylammonium chloride and 300 ml of toluene was stirred at 60° C. for 24 hours. The reaction mixture was washed with water, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure. The residue was subjected to silica gel (550 g) column chromatography, and eluted with hexane-ethyl acetate (30:1), to give 1,2-epoxy-3-(12-cyclohexyldodecyloxy)propane as colorless oil.

Workup

washThe reaction mixture was washed with water
dry with materialdried (anhydrous magnesium sulfate)
concentrationconcentrated under reduced pressure
washeluted with hexane-ethyl acetate (30:1)

Sources & evidence

ORD record: ord-e24d3128de0947ce9d240555e39869e5
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04889953

Linked notes

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