Ethylene Glycol → HCID 70372852, compound

HRID 903200Notes

Reaction equation

HRID 903200 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].O.[C:6]1(C)[CH:11]=[CH:10][C:9](S(O)(=O)=O)=[CH:8][CH:7]=1.C1C=CC=CC=1>O>[CH2:2]1[CH2:1][O:4][CH2:9][CH:10]([CH2:11][CH2:6][CH:7]=[CH2:8])[O:3]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 70372852HCID 70372852, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-oxy-1-hexene (9.8 g.), ethylene glycol (18.6 g.), p-toluene sulfonic acid monohydrate (1.56 g.) and benzene (250 ml.) is heated at reflux under a Dean-Stark water separator. After 2 hrs., the reaction mixture is washed with water and the organic layer is separated, dried with magnesium, and evaporated in vacuo. Distillation of the residue gives 5-ethylenedioxy-1-hexene (90% yield) b.p. 34°-37°/1.5 mm. nmr (CDCl3)δ: 1.27 (s, CH3), 1.5-2.4 (m, CH2 --CH2); 2.83 (s, --O--CH2 --CH2 --O); 4.80-6.1 (m, CH2 =CH--). IR (film)μ: 6.06 (CH2 =CH--).

Workup

  1. temperatureis heated
  2. wash, the reaction mixture is washed with water
  3. customthe organic layer is separated
  4. dry with materialdried with magnesium
  5. customevaporated in vacuo
  6. distillationDistillation of the residue

Sources & evidence

ORD record
ord-08d1a18d4aa448e392edc03879df4651
Source dataset
uspto-grants-1980_10
Patent number
US04226866

Reaction notes

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