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

HRID 1165103Notes

Reaction equation

HRID 1165103 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(OC)(OC)OC>>[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

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 9005Trimethyl orthoformate2×HCID 691504,4'-Dihydroxybenzophenone

Product 1

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

Procedure

2,2-bis(4-hydroxyphenyl)-1,3-dioxolane was prepared by the procedure of Example 5 by mixing together, in a reaction flask fitted with a mechanical stirrer, thermometer, and variable take-off distillation head, 99 gm of 4,4'-dihydroxybenzophenone (97% pure, 0.448 mole), 269 gm of ethylene glycol (4.3 moles), 96 gm of trimethyl orthoformate (0.91 mole), and 150 gm of montmorillonite clay (K-10, United Catalysts) and heating the reaction mixture at 70° to 90° to give slow distillation of the reaction by-products. After about 18 hours, 66 gm of distillate had been collected, an additional 64 gm of trimethylorthoformate (0.60 mole) was added to the reaction mixture, and the reaction continued. After a total of 24 hours reaction time, NMR analysis of a reaction sample showed about 2.23 mole ratio of ketal product to ketone starting material; after a total of 48 hours reaction time, NMR analysis of a second reaction sample showed the mole ratio was about 19 (about 95% conversion to ketal product). The reaction mixture was heated for an additional 8 hours and then cooled; NMR analysis again showed about 95% conversion.

Workup

  1. additionby mixing together, in a reaction flask
  2. customfitted with a mechanical stirrer
  3. temperatureheating the reaction mixture at 70° to 90°
  4. customto give slow
  5. distillationdistillation of the reaction by-products
  6. distillation66 gm of distillate had been collected
  7. customAfter a total of 24 hours reaction time, NMR analysis of a reaction sample
  8. customafter a total of 48 hours reaction time, NMR analysis of a second reaction sample
  9. temperatureThe reaction mixture was heated for an additional 8 hours
  10. temperaturecooled

Sources & evidence

ORD record
ord-cef1f136bf55417ba2dc9c4a7d8d4555
Source dataset
uspto-grants-1990_03
Patent number
US04906786

Reaction notes

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