Ethylene Glycol → HCID 19874512, compound

HRID 465454Notes

Reaction equation

HRID 465454 reaction equation
[C:1]1([CH2:11][C:12](=[O:14])[CH3:13])[CH:6]=[CH:5][C:4]([CH2:7][C:8](=[O:10])[CH3:9])=[CH:3][CH:2]=1.[CH2:15](O)[CH2:16][OH:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:15]1[CH2:16][O:17][C:12]([CH3:13])([CH2:11][C:1]2[CH:2]=[CH:3][C:4]([CH2:7][C:8](=[O:10])[CH3:9])=[CH:5][CH:6]=2)[O:14]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 11263975HCID 11263975, compound

Product 1

HCID 19874512HCID 19874512, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1,4-phenylene bis(propan-2-one), (17.12 g), ethane-1,2-diol (1.72 g) and a trace of 4-toluene sulphonic acid was heated under reflux in benzene for 2 hr. using a Dean and Stark apparatus. The solvent was evaporated and the residue chromatographed on silica. Elution with 1:3 diethyl ether:petrolroleum ether (40-60) gave 4-(2,2-(ethylenedioxy)propyl)phenyl propan-2-one, as a white solid (3.5 g). Further elution gave starting material (12.9 g).

Workup

  1. customThe solvent was evaporated
  2. customthe residue chromatographed on silica
  3. washElution with 1:3 diethyl ether

Sources & evidence

ORD record
ord-6e619ce348ae4cc18263e8d65e6f6d83
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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