Ethylene Glycol → 4,4'-(1,3-Dioxolane-2,2-diyl)diphenol

HRID 876131Notes

Reaction equation

HRID 876131 reaction equation
O[C:2]1[C:3](O)=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11]C=[CH:9][CH:8]=1)=O.[CH2:17]([OH:20])[CH2:18][OH:19].[CH:21]([O-:25])([O-])OC.C(OCC)(=[O:28])C>>[OH:28][C:15]1[CH:2]=[CH:3][C:4]([C:5]2([C:7]3[CH:8]=[CH:9][C:21]([OH:25])=[CH:11][CH:12]=3)[O:20][CH2:17][CH2:18][O:19]2)=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 8857Ethyl AcetateHCID 12416099(2,3-Dihydroxyphenyl)(phenyl)methanoneHCID 53629101Methylorthoformate2×

Product 1

HCID 147659554,4'-(1,3-Dioxolane-2,2-diyl)diphenol

Procedure

In a flask equipped with a stirring blade and a thermometer, montmorillonite clay K10 (150 g) and 99 g of dihydroxybenzophenone were charged and the atmosphere in the flask was replaced by nitrogen. 242 mL of ethylene glycol and 99 mL of methyl orthoformate were added and the reaction was carried out at 110° C. while distilling of by-products produced. After 18 hours, 66 g of methyl orthoformate was added and the reaction was carried out for additional 30 hours, namely, 48 hours in total. The reaction solution was diluted with 300 mL of ethyl acetate added, filtered and then extracted with an aqueous 2% sodium hydrogen carbonate solution four times. The extract solution was concentrated and then recrystallized from dichloroethane to obtain the objective 2,2-bis(4-hydroxyphenyl)-1,3-dioxolane. From gas chromatography, the purity was found to be 99.5%.

Workup

  1. customIn a flask equipped with a stirring blade
  2. customwas carried out at 110° C.
  3. distillationwhile distilling of by-products
  4. customproduced
  5. waitthe reaction was carried out for additional 30 hours
  6. custom48 hours
  7. additionadded
  8. filtrationfiltered
  9. extractionextracted with an aqueous 2% sodium hydrogen carbonate solution four times
  10. concentrationThe extract solution was concentrated
  11. customrecrystallized from dichloroethane

Sources & evidence

ORD record
ord-22d75ad2c92746df954bd97ac4f76bea
Source dataset
uspto-grants-2015_03
Patent number
US08986903B2

Reaction notes

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