Epichlorohydrin → 1,5-Dimethyl-2-[3-(2,3-epoxypropoxy)-phenyl]-pyrrole

HRID 638066Notes

Reaction equation

HRID 638066 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][CH:4]=[C:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21]([CH:23]1[O:25][CH2:24]1)Cl>>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][CH:4]=[C:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:21][CH:23]2[O:25][CH2:24]2)[CH:9]=1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 202551681,5-Dimethyl-2-(3-hydroxyphenyl)-pyrrole

Product 1

HCID 202551361,5-Dimethyl-2-[3-(2,3-epoxypropoxy)-phenyl]-pyrrole

Procedure

While stirring, a mixture of 10 g of the resulting crude 1,5-dimethyl-2-(3-hydroxyphenyl)-pyrrole, 50 ml of epichlorohydrin and 15.2 g of potassium carbonate is heated at boiling point for 3 hours. The reaction mixture is cooled, filtered and concentrated by evaporation. The residue is divided between 200 ml of ether and 20 ml of 2N sodium hydroxide solution; the ether phase is separated off, dried over magnesium sulphate and concentrated by evaporation. The crude 1,5-dimethyl-2-[3-(2,3-epoxypropoxy)-phenyl]-pyrrole is obtained in the form of an oil and is further used in that form.

Workup

  1. temperatureis heated
  2. customfor 3 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customthe ether phase is separated off
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1ef0c8ba247b4bc3891994ddb290965c
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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