Epichlorohydrin → 1-{2-[(Oxiran-2-yl)methoxy]phenyl}-1H-pyrrole

HRID 1287317Notes

Reaction equation

HRID 1287317 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])[CH:5]=[CH:4][CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([CH:21]1[O:23][CH2:22]1)Cl>>[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][CH2:19][CH:21]2[O:23][CH2:22]2)[CH:2]=[CH:3][CH:4]=[CH:5]1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 7123342-(1H-Pyrrol-1-Yl)Phenol

Product 1

HCID 137555101-{2-[(Oxiran-2-yl)methoxy]phenyl}-1H-pyrrole

Procedure

95.7 g of o-(pyrrol-1-yl)-phenol, 245 g of potassium carbonate and 167 g of epichlorohydrin are heated to the boil in a nitrogen atmosphere, whilst stirring. After 6 hours, the reaction mixture is cooled and filtered and the filtrate is evaporated in vacuo, ultimately at a bath temperature of 120° C. The oil which remains is dissolved in 300 ml of ether and the solution is extracted with 300 ml of 2 N sodium hydroxide solution and washed with 100 ml of water. The oil which remains after evaporating off the solvent is distilled in a high vacuum and gives 1-[o-(pyrrol-1-yl)-phenoxy]-2,3-epoxy-propane of boiling point 103°-105° C/0.001 mm Hg.

Workup

  1. temperaturethe reaction mixture is cooled
  2. filtrationfiltered
  3. customthe filtrate is evaporated in vacuo, ultimately at a bath temperature of 120° C
  4. dissolutionThe oil which remains is dissolved in 300 ml of ether
  5. extractionthe solution is extracted with 300 ml of 2 N sodium hydroxide solution
  6. washwashed with 100 ml of water
  7. customafter evaporating off the solvent
  8. distillationis distilled in a high vacuum

Sources & evidence

ORD record
ord-2028f0fe27ac4ef8a1dba9f9bc591004
Source dataset
uspto-grants-1976_10
Patent number
US03984436

Reaction notes

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