Acetic Acid → HCID 14722844, compound

HRID 478023Notes

Reaction equation

HRID 478023 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[CH:8][C:9]=1[OH:10])=[O:3].[C:12]([OH:15])(=[O:14])[CH3:13].[CH3:16]N(C=O)C>C[O-].[Na+].CO>[OH:11][C:7]1[CH:6]=[CH:5][C:4]2[C:2](=[O:3])[CH:1]=[C:13]([C:12]([O:15][CH3:16])=[O:14])[O:10][C:9]=2[CH:8]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 69902',4'-Dihydroxyacetophenone

Product 1

HCID 14722844HCID 14722844, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

2,4-dihydroxyacetophenone (7.1 g, 0.05 mol) and dimethyl oxylate (7.2 g) were dissolved in DMF containing a solution of sodium methoxide in methanol (4.0 g Na, 100 ml MeOH) and the mixture was stirred at room temperature for 48 hours. At this point, acetic acid (180 ml) was added and the mixture was heated to 100° C. for 5 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was separated, the aqueous layer was thoroughly extracted with more ethyl acetate, and the combined organic extracts were washed with brine. Evaporation of the dried (Na2SO4) solvent in vacuo afforded methyl 7-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate (6a) as a crude yellow solid which was crystallized from from ethyl acetate/hexane to afford 3.5 g of pure product.

Workup

  1. temperaturethe mixture was heated to 100° C. for 5 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was thoroughly extracted with more ethyl acetate
  6. washthe combined organic extracts were washed with brine
  7. customEvaporation of the
  8. dry with materialdried (Na2SO4) solvent in vacuo

Sources & evidence

ORD record
ord-78afa80a9a014c4b9fed22e36921bc9f
Source dataset
uspto-grants-1989_12
Patent number
US04889871

Reaction notes

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