Ethylene Glycol → HCID 57296787, compound

HRID 435065Notes

Reaction equation

HRID 435065 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6](=O)[CH2:5][C:4]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH3:9])[O:3]1.[CH2:20]([OH:23])[CH2:21][OH:22].[C:24]1(C)C=CC(S(O)(=O)=O)=C[CH:25]=1>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:19])[CH:6]([CH:21]2[CH2:20][O:23][CH2:25][CH2:24][O:22]2)[CH2:5][C:4]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH3:9])[O:3]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 20490674HCID 20490674, compound

Product 1

HCID 57296787HCID 57296787, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1 g of the ketone of Example 6, 250 mg of ethylene glycol and a few milligrams of para-toluenesulphonic acid in 20 ml benzene were heated at reflux temperature in a Dean/Stark apparatus for 16 hours. The resulting mixture was washed with aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated to give 1.16 g crude material which was purified on a silica gel column using 3% acetone in petrol as eluant to give 1.0 g (86%) of the desired product.

Workup

  1. temperatureat reflux temperature in a Dean/Stark apparatus for 16 hours
  2. washThe resulting mixture was washed with aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customto give 1.16 g crude material which
  6. customwas purified on a silica gel column

Sources & evidence

ORD record
ord-8e65c54c9c5c42319c0ec669e198fcb2
Source dataset
uspto-grants-1983_08
Patent number
US04400198

Reaction notes

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