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

HRID 2174174Notes

Reaction equation

HRID 2174174 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.C([O:22][CH3:23])(OC)OC.C(OCC)(=[O:26])C.[CH2:30]([OH:33])[CH2:31][OH:32]>>[OH:26][C:15]1[CH:2]=[CH:3][C:4]([C:5]2([C:7]3[CH:8]=[CH:9][C:23]([OH:22])=[CH:11][CH:12]=3)[O:33][CH2:30][CH2:31][O:32]2)=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 8857Ethyl AcetateHCID 9005Trimethyl orthoformateHCID 12416099(2,3-Dihydroxyphenyl)(phenyl)methanone

Product 1

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

Procedure

Montmorillonite clay K10 (150 g) was reacted with 99 g of dihydroxybenzophenone at 110° C. in a mixture of 242 ml of ethylene glycol/99 ml of trimethyl orthoformate while distilling a produced by-product. After a lapse of 18 hours, 66 g of trimethyl orthoformate was added to perform a synthetic reaction for 48 hours. 300 ml of ethyl acetate was added to a reactant solution, and the resulting mixture was filtered and extracted with a 2% aqueous solution of sodium hydrogen carbonate four times. Furthermore, the reactant was concentrated, and then recrystallized with dichloroethane to obtain desired 2,2-bis(4-hydroxyphenyl)-1,3-dioxolane.

Workup

  1. distillationwhile distilling a produced by-product
  2. additionAfter a lapse of 18 hours, 66 g of trimethyl orthoformate was added
  3. customa synthetic reaction for 48 hours
  4. filtrationthe resulting mixture was filtered
  5. extractionextracted with a 2% aqueous solution of sodium hydrogen carbonate four times
  6. concentrationFurthermore, the reactant was concentrated
  7. customrecrystallized with dichloroethane

Sources & evidence

ORD record
ord-7ac264f172d5464d814b7a2827ebf2ae
Source dataset
uspto-grants-2015_06
Patent number
US09059448B2

Reaction notes

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