Ethylene Glycol → HCID 86633363, compound

HRID 876130Notes

Reaction equation

HRID 876130 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:17](O)[CH2:18][OH:19].C([O-])([O-])OC>C(OCC)(=O)C>[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]2([C:8]3[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=3)[O:19][CH2:18][CH2:17][O:7]2)=[CH:4][CH:3]=1.[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 691504,4'-DihydroxybenzophenoneHCID 53629101Methylorthoformate2×

Product 1

HCID 86633363HCID 86633363, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a flask equipped with a stirring blade and a thermometer, montmorillonite clay K10 (750 g) and 495 g of 4,4′-dihydroxybenzophenone were charged, and the atmosphere in the flask was replaced by nitrogen. 1,200 mL of ethylene glycol and 500 mL of methyl orthoformate were added and the reaction was carried out at a bath temperature of 110° C. for 8 hours while distilling off by-products produced. 500 mL of methyl orthoformate was added, followed by the reaction for 8 hours, namely, 16 hours in total. The reaction solution was diluted by adding 1 L of ethyl acetate and clay was removed by filtration, and then solution was extracted with an aqueous 2% sodium hydrogen carbonate solution four times. The extract solution was concentrated and the resulting slurry-like compound was washed with dichloroethane to obtain a 2,2-bis(4-hydroxyphenyl)-1,3-dioxolane/4,4′-dihydroxybenzophenone mixture (=85.5/14.5 mol %). The structure was confirmed by 1H-NMR. Other impurities could not be recognized by gas chromatography.

Workup

  1. customIn a flask equipped with a stirring blade
  2. customthe reaction was carried out at a bath
  3. distillationtemperature of 110° C. for 8 hours while distilling off by-products
  4. customproduced
  5. customfollowed by the reaction for 8 hours
  6. custom16 hours
  7. additionThe reaction solution was diluted
  8. customwas removed by filtration
  9. extractionsolution was extracted with an aqueous 2% sodium hydrogen carbonate solution four times
  10. concentrationThe extract solution was concentrated
  11. washthe resulting slurry-like compound was washed with dichloroethane

Sources & evidence

ORD record
ord-9180793486304916a55050dac7f3fe5f
Source dataset
uspto-grants-2015_03
Patent number
US08986903B2

Reaction notes

Loading…