1-Bromo-3-chloropropane → 4H-1-Benzopyran-4-one, 7-(3-chloropropoxy)-

HRID 2118485Notes

Reaction equation

HRID 2118485 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6](=[O:10])[CH:7]=[CH:8][O:9][C:4]=2[CH:3]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6](=[O:10])[CH:7]=[CH:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 54092797-Hydroxy-4-benzopyrone

Product 1

HCID 108475634H-1-Benzopyran-4-one, 7-(3-chloropropoxy)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-hydroxy-4H-1-benzopyran-4-one, VII (40.5 g; 0.25 mole; prepared according to G. N. Dorafeenko and V. V. Tkachenko, Chem. Heterocyclic Compounds, 1972 (8) 935), 1-bromo-3-chloropropane (78.5 g; 0.50 mole) and anhydrous potassium carbonate (49 g; 0.50 mole) in 1000 ml of acetone was heated at reflux for 16 hours. The mixture was filtered through celite and concentrated in vacuo. The thick red oil which remained was triturated with ether, upon which 57.8 g (97%) of the title compound was obtained, mp 72°-73° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe mixture was filtered through celite and
  4. concentrationconcentrated in vacuo
  5. customThe thick red oil which remained was triturated with ether, upon which 57.8 g (97%) of the title compound
  6. customwas obtained

Sources & evidence

ORD record
ord-095c5a9f81b54bcbb4be8418f770785f
Source dataset
uspto-grants-1987_07
Patent number
US04678787

Reaction notes

Loading…