Hydrochloric Acid → 4-oxo-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

HRID 1079304Notes

Reaction equation

HRID 1079304 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[O:5].Cl>C(=O)([O-])[O-].[Na+].[Na+]>[O:5]=[C:4]1[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=2[O:1][CH:7]([C:8]([OH:10])=[O:9])[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 554933-(2-Hydroxybenzoyl)acrylic acid

Product 1

HCID 98557084-oxo-3,4-dihydro-2H-1-benzopyran-2-carboxylic acidYield 67%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

A solution of 3-(2-hydroxybenzoyl)acrylic acid (3.02 g) in aqueous sodium carbonate (5%, 55 ml) was stirred at room temperature for 15 hours, acidified with 2N HCl and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then treated with activated charcoal, after which the solvent was distilled off, to yield 2,3-dihydro-4-oxo-4H-1-benzopyran-2-carboxylic acid (2.01 g, 67%), which was then recrystallized from ethyl acetate-hexane to yield colorless prisms having a melting point of 170° to 171° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. additiontreated with activated charcoal
  5. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-70da9981d0d4431ab58985a45bb26647
Source dataset
uspto-grants-1996_12
Patent number
US05580863

Reaction notes

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