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

HRID 1097
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 1969464710-(2-Ethylhexyloxy)decanol

Product 1

HCID 1969463510-(2-Ethylhexyloxy)decyl glycidyl etherYield 82.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst
HCID 8058
Hexane
Solvent

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

  1. customA 200-ml flask equipped with a stirrer
  2. temperaturereflux tube
  3. customAfter the resultant reaction mixture
  4. washwas washed with water
  5. distillationthe solvent was distilled off under reduced pressure
  6. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes