Epichlorohydrin → HCID 21518636, compound

HRID 1283645Notes

Reaction equation

HRID 1283645 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])[CH2:2][CH2:3][CH3:4].[CH2:23]([CH:25]1[O:27][CH2:26]1)Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:23][CH:25]1[O:27][CH2:26]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 22596121HCID 22596121, compound

Product 1

HCID 21518636HCID 21518636, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.5 g. (0.025 mol.) of 2-n-butyl-3-(2'-hydroxybenzoyl)benzofuran, 25 ml. of epichlorohydrin and 15.0 g. of potassium carbonate in 150 ml. of ethanol was refluxed for three hours. After cooling the reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water and the aqueous solution was extracted with methylene chloride. The extracts were combined, dried (Na2SO4) and concentrated to give an oily residue that was chromatographed on alumina with chloroform as the eluant to give 2-n-butyl-3-[2'-(2,3-epoxy)propoxybenzoyl]benzofuran.

Workup

  1. additionA mixture of 7.5 g
  2. temperatureAfter cooling the reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in water
  6. extractionthe aqueous solution was extracted with methylene chloride
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto give an oily residue that
  10. customwas chromatographed on alumina with chloroform as the eluant

Sources & evidence

ORD record
ord-0dc9186df59d4e7c9d898b555b414a2f
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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