Ethylene Glycol → 2-(1,1-Dimethylethyl)-2-(4-carboxyphenyl)-1,3-dioxolane

HRID 1768670Notes

Reaction equation

HRID 1768670 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=[O:4].[CH2:16](O)[CH2:17][OH:18].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]([C:3]1([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)[O:18][CH2:17][CH2:16][O:4]1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 69252-Methylbenzenesulfonic acidHCID 119589814-(2,2-Dimethyl-1-oxopropyl)benzoic acid

Product 1

HCID 152328382-(1,1-Dimethylethyl)-2-(4-carboxyphenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 63.5 grams (0.31 mole) of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid, 156 ml. of ethylene glycol, and 1 gram of toluenesulfonic acid in 600 ml of toluene is refluxed for 24 hours using a Dean-Stark trap to remove water. The mixture is then cooled and partially evaporated; and to the residue, 4.5 grams of solid potassium hydroxide are carefully added followed by 225 ml of water. The resulting mixture is refluxed for 11/2 hours, cooled, filtered and the layers separated. The aqueous layer is acidified with 2N hydrochloric acid, and the resulting precipitate is removed by filtration. The precipitate is washed with water, then water/ethanol (5/1), and then petroleum ether. The product is dried in vacuo to yield the title product (m.p. 213.5°-215.5° C.).

Workup

  1. customto remove water
  2. temperatureThe mixture is then cooled
  3. custompartially evaporated
  4. additionand to the residue, 4.5 grams of solid potassium hydroxide are carefully added
  5. temperatureThe resulting mixture is refluxed for 11/2 hours
  6. temperaturecooled
  7. filtrationfiltered
  8. customthe layers separated
  9. customthe resulting precipitate is removed by filtration
  10. washThe precipitate is washed with water
  11. customThe product is dried in vacuo

Sources & evidence

ORD record
ord-3f02a58871084aa484881ad98472ad37
Source dataset
uspto-grants-1995_01
Patent number
US05378728

Reaction notes

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