Methane → 2H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-

HRID 1193654Notes

Reaction equation

HRID 1193654 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+].C>CC(C)=O.CC(O)C>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8](=[O:12])[O:9][C:10]=2[CH:11]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 5281426Umbelliferone

Product 1

HCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 16.8 g (0.104 mole) of 7-hydroxycoumarin, 31.6 g (0.2 mole) of 1-bromo-3-chloropropane and 41.5 g (0.3 mole) of anhydrous potassium carbonate in 500 ml of acetone was heated at reflux for 24 hr. The mixture was filtered with difficulty to give a milky filtrate. The filtrate was treated wich charcoal and filtered through celite to give a clear filtrate. The filtrate was concentrated under reduced pressure to give a solid residue. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration, and dried to yield 19.1 g (77%) of fluffy, white solid. An analytical sample, m.p. 100°-102° C., was obtained on recrystallization from 2-propanol.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. filtrationThe mixture was filtered with difficulty
  4. customto give a milky filtrate
  5. filtrationfiltered through celite
  6. customto give a clear filtrate
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give a solid residue
  9. customThe solid was triturated with petroleum ether (30°-60° C.)
  10. filtrationcollected by filtration
  11. customdried
  12. customto yield 19.1 g (77%) of fluffy, white solid

Sources & evidence

ORD record
ord-5e552d0d81b04e2ab10993f605905cce
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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