Ethylene Glycol → 2-(3-Cyclohexylpropyloxy)-ethanol

HRID 1388153Notes

Reaction equation

HRID 1388153 reaction equation
[Na].[CH:2]1([CH2:8][CH2:9][CH2:10]Br)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O.[CH2:13]([OH:16])[CH2:14][OH:15]>C1(C)C(C)=CC=CC=1>[CH:2]1([CH2:8][CH2:9][CH2:10][O:15][CH2:14][CH2:13][OH:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 96426(3-Bromopropyl)cyclohexaneHCID 5360545Sodium

Product 1

HCID 204717772-(3-Cyclohexylpropyloxy)-ethanolYield 82.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
100 °C

Procedure

85 ml of xylene are added to a solution of 15.75 g of sodium in 182.2 g of ethylene glycol. The mixture is heated to 100° C., and a solution of 140.5 g of 3-cyclohexylpropyl bromide in 70 ml of xylene is added dropwise within 3 hours. When the addition has ended, the mixture is boiled for 4 hours under reflux, cooled, and then 500 ml of water are added. The mixture is extracted with twice 500 ml of petroleum ether, the combined organic phases are dried over sodium sulphate and the remaining oil is purified by chromatography on silica gel (migrating agent: 80:20 petroleum ether/ethyl acetate). 105.3 g of 2-(3-cyclohexylpropyloxy)-ethanol are obtained.

Workup

  1. additionWhen the addition
  2. temperatureunder reflux
  3. temperaturecooled
  4. extractionThe mixture is extracted with twice 500 ml of petroleum ether
  5. dry with materialthe combined organic phases are dried over sodium sulphate
  6. customthe remaining oil is purified by chromatography on silica gel (migrating agent: 80:20 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-3bd868d56e3a4e17a0e78be73aaf9d55
Source dataset
uspto-grants-1984_02
Patent number
US04430339

Reaction notes

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