Ethylene Glycol → HCID 13214222, compound

HRID 1018499Notes

Reaction equation

HRID 1018499 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH2:20](O)[CH2:21][OH:22].O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH2:3][C:4]2([CH2:5][CH2:6][CH:7]=1)[O:22][CH2:21][CH2:20][O:8]2

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 69252-Methylbenzenesulfonic acidHCID 145113-Methyl-2-cyclohexen-1-one

Product 1

HCID 13214222HCID 13214222, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-methyl-2-cyclohexenone (4 g, 36.36 mmol), toluenesulfonic acid (100 mg) and ethylene glycol (7 mL) in 100 mL of toluene is refluxed overnight and water formed is removed by Dean-Stark trap. The residue after concentration is chromatographed on silica gel (10% ethyl acetate/hexane) to give 3.36 g (62%) of 7-methyl-1,4-dioxa-spiro[4.5]dec-7-ene.

Workup

  1. temperatureis refluxed overnight
  2. customis removed by Dean-Stark trap
  3. concentrationThe residue after concentration
  4. customis chromatographed on silica gel (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-79842ae9c2fd48b29dc5761ff31c4ee3
Source dataset
uspto-grants-2002_11
Patent number
US06482834B2

Reaction notes

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