Sodium Bicarbonate → 4-oxo-7-(3-[2-propylphenoxy]propoxy)-4H-1-benzopyran-2-carboxylic acid

HRID 435861Notes

Reaction equation

HRID 435861 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:23][CH2:24][CH3:25])=[CH:11][C:6]=2[O:5][C:4]([C:26]([O:28]CC)=[O:27])=[CH:3]1.C(=O)(O)[O-].[Na+]>C(O)C>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:23][CH2:24][CH3:25])=[CH:11][C:6]=2[O:5][C:4]([C:26]([OH:28])=[O:27])=[CH:3]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 13090997ethyl 4-oxo-7-(3-[2-propylphenoxy]-propoxy)-4H-1-benzopyran-2-carboxylate

Product 1

HCID 130909874-oxo-7-(3-[2-propylphenoxy]propoxy)-4H-1-benzopyran-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.05 parts of ethyl 4-oxo-7-(3-[2-propylphenoxy]-propoxy)- 4H-1-benzopyran-2-carboxylate and 0.46 parts of sodium bicarbonate in 100 parts of 50% v/v aqueous ethanol was stirred on a steam bath for three hours, then cooled and extracted with ether. The aqueous extract was acidified with excess 2N hydrochloric acid to give a white precipitate which was collected, washed with water and dried. Crystallisation of this solid from acetone gave 1.01 parts of 4-oxo-7-(3-[2-propylphenoxy]propoxy)-4H-1-benzopyran-2-carboxylic acid, m.pt. 168°-171°.

Workup

  1. temperaturecooled
  2. extractionextracted with ether
  3. extractionThe aqueous extract
  4. customto give a white precipitate which
  5. customwas collected
  6. washwashed with water
  7. customdried
  8. customCrystallisation of this solid from acetone

Sources & evidence

ORD record
ord-e4c8c8b3fa454f6eaeeb303508fabddf
Source dataset
uspto-grants-1977_02
Patent number
US04006245

Reaction notes

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