Potassium Hydroxide → 10-(2-Ethylhexyloxy)decanol

HRID 1096

Reaction equation

HRID 1096 reaction equation
[CH2:1]([OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[OH-].[K+].[CH2:15]([CH:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18]Br)[CH3:16]>C1(C)C(C)=CC=CC=1>[CH2:15]([CH:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH3:16]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 371531,10-DecanediolHCID 868042-Ethylhexyl bromide

Product 1

HCID 1969464710-(2-Ethylhexyloxy)decanolYield 72.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A 1-liter flask equipped with a stirrer and distiller was charged with 25 g (0.14 mol) of 1,10-decanediol, 8.09 g (0.14 mol) of KOH and 300 ml of xylene, and the resultant mixture was heated at 120° C. for 1 hour, thereby distilling off water formed. To this reaction mixture, were added 23.1 g (0.12 mol) of 2-ethylhexyl bromide, and the resulting mixture was heated and stirred for 15 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and washed with water. After the solvent was distilled off under reduced pressure, the resulting residue was purified by column chromatography on silica gel, thereby obtaining 24.8 g (yield: 72%) of 10-(2-ethylhexyloxy)decanol.

Workup

  1. customA 1-liter flask equipped with a stirrer
  2. distillationdistilling off water
  3. customformed
  4. temperaturethe resulting mixture was heated
  5. customAfter completion of the reaction
  6. washwashed with water
  7. distillationAfter the solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-31b708e4b55e4146a82a5bb5a9af3de8
Source dataset
uspto-grants-1998_03
Patent number
US05723497

Linked notes

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