Potassium Carbonate → HCID 20535634, compound

HRID 1156227Notes

Reaction equation

HRID 1156227 reaction equation
[OH:1][C:2]1[C:7]2[C:8](=[O:17])[CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:11][C:6]=2[C:5]([CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1.[OH:21][CH:22]([CH3:25])[CH2:23]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:21][CH:22]([CH3:25])[CH2:23][O:1][C:2]1[C:7]2[C:8](=[O:17])[CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:11][C:6]=2[C:5]([CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 297401-Bromo-2-propanolHCID 13226751HCID 13226751, compound

Product 1

HCID 20535634HCID 20535634, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 5-hydroxy-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylate (2.2 g), 2-hydroxy propyl bromide (5 g), anhydrous potassium carbonate (5 g) and acetone (200 ml) was heated at reflux for 3 days. After cooling, the reaction mixture was filtered and the acetone removed from the filtrate in vacuo. The oily residue was dissolved in chloroform (100 ml) and the chloroform solution washed with 1 N aqueous sodium hydroxide solution (50 ml) and water (50 ml) and then dried. Removal of the chloroform in vacuo gave a brown solid which on crystallisation from ethanol gave ethyl 5-(2-hydroxypropoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylate identical in all respects with authentic material.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 days
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customthe acetone removed from the filtrate in vacuo
  6. dissolutionThe oily residue was dissolved in chloroform (100 ml)
  7. washthe chloroform solution washed with 1 N aqueous sodium hydroxide solution (50 ml) and water (50 ml)
  8. customdried
  9. customRemoval of the chloroform in vacuo
  10. customgave a brown solid which
  11. customon crystallisation from ethanol

Sources & evidence

ORD record
ord-13103ec1b506403087665757a4b394e1
Source dataset
uspto-grants-1982_06
Patent number
US04335048

Reaction notes

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