Epichlorohydrin → 10-(2-Ethylhexyloxy)decyl glycidyl ether

HRID 1097

Reaction equation

[CH2:1]([CH:3]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[CH3:2].[CH2:21]([CH:23]1[O:25][CH2:24]1)Cl.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[CH2:21]([O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:17][CH2:18][CH2:19][CH3:20])[CH:23]1[O:25][CH2:24]1

Participants

Conditions

Temperature: 40 °C

Procedure

A 200-ml flask equipped with a stirrer, reflux tube and dropping funnel was charged with 24.8 g (87 mmol) of 10-(2-ethylhexyloxy)decanol, 17.7 g (0.191 mol) of epichlorohydrin, 1.4 g (4.4 mmol) of tetrabutylammonium bromide and 25 ml of hexane. While stirring the mixture at 40° C., 29.2 g (0.35 mol) of a 48% aqueous solution of NaOH were added dropwise over 3 hours. After completion of the dropping, the stirring was continued further for 2 hours at 40° C. After the resultant reaction mixture was washed with water, and the solvent was distilled off under reduced pressure, the resultant residue was purified by column chromatography on silica gel, thereby obtaining 24.6 g (yield: 82.6%) of 10-(2-ethylhexyloxy)decyl glycidyl ether.

Workup

customA 200-ml flask equipped with a stirrer
temperaturereflux tube
customAfter the resultant reaction mixture
washwas washed with water
distillationthe solvent was distilled off under reduced pressure
customthe resultant residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-aca60743900142f7968a0bb1a46a2668
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723497

Linked notes

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