Ethylene Glycol → 2-(4-bromophenyl)-2-phenyl-1,3-dioxolane

HRID 2072450Notes

Reaction equation

HRID 2072450 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:16](O)[CH2:17][OH:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:9]1([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)[O:18][CH2:17][CH2:16][O:15]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 70304-Bromobenzophenone

Product 1

HCID 38475232-(4-bromophenyl)-2-phenyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 1300 milliliters of toluene in a flask equipped with a Dean-Stark tube are dissolved 100 grams of p-bromobenzophenone; and to this solution is added 150 grams of ethyleneglycol and 4.4 grams of p-toluenesulphonic acid. This mixture is refluxed until no further water collects in the Dean-Stark tube. After distilling off the toluene and recrystallization from methanol one obtains 2-phenyl-2-(p-bromophenyl)-1,3-dioxolane.

Workup

  1. distillationAfter distilling off
  2. customthe toluene and recrystallization from methanol one

Sources & evidence

ORD record
ord-6b948675d9ec46a8afc8827ceeda5e9c
Source dataset
uspto-grants-1977_09
Patent number
US04051261

Reaction notes

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