Potassium Carbonate → 2-[4'-(2,3-Epoxypropoxy)phenyl]-3-(4'-methylbenzoyl)benzofuran

HRID 1414621Notes

Reaction equation

HRID 1414621 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=3[C:12]=2[C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[CH2:26]([CH:28]1[O:30][CH2:29]1)Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:30]1[CH2:29][CH:28]1[CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=3[C:12]=2[C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 214879512-p-Hydroxyphenyl-3-p-methylbenzoylbenzofuran

Product 1

HCID 214880322-[4'-(2,3-Epoxypropoxy)phenyl]-3-(4'-methylbenzoyl)benzofuran

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.0 g. (6.1 mmol.) of 2-p-hydroxyphenyl-3-p-methylbenzoylbenzofuran, 2.6 g. (0.019 mol.) of epibromohydrin and 3.0 g. (0.021 mol.) of potassium carbonate in 100 ml. of dry acetone was refluxed for 12 hours. After cooling, the reaction mixture was filtered and the filtrate was concentrated to give 2-[4'-(2,3-epoxypropoxy)phenyl]-3-(4'-methylbenzoyl)benzofuran.

Workup

  1. additionA mixture of 2.0 g
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cef56caa2ece4fca8e8400a88e035fbc
Source dataset
uspto-grants-1977_01
Patent number
US04001426

Reaction notes

Loading…