Acetic Acid → 2-Carbomethoxy-7-hydroxy-8-propylchromone

HRID 477512Notes

Reaction equation

HRID 477512 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].[C:15](OC)(=O)[C:16]([O:18][CH3:19])=[O:17].C[O-].[Na+].C(O)(=O)C>CN(C)C=O>[OH:14][C:5]1[CH:6]=[CH:7][C:8]2[C:11](=[O:12])[CH:13]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[O:10][C:9]=2[C:4]=1[CH2:3][CH2:2][CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11120Dimethyl oxalateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 139207782-Carbomethoxy-7-hydroxy-8-propylchromoneYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 99.7 g (0.513 mole) of 2,4-dihydroxy-3-propylacetophenone and 72.7 g (0.77 mole) of dimethyl oxalate in 1 liter of dry dimethylformamide was added in portions 97 g (1.8 mmole) of sodium methoxide. After stirring for 4 hours, 1.8 l of acetic acid was added and stirring was continued for 4 days. The reaction mixture was heated in a steam bath for four hours and evaporated to dryness. Water was added to the residue and the mixture was heated to boiling. A solid was filtered off and recrystallized from ethanol to give 89.8 g of the title compound, mp. 222°-224°. Structure assignment was supported by nmr and infrared spectra.

Workup

  1. stirringstirring
  2. waitwas continued for 4 days
  3. temperatureThe reaction mixture was heated in a steam bath for four hours
  4. customevaporated to dryness
  5. additionWater was added to the residue
  6. temperaturethe mixture was heated to boiling
  7. filtrationA solid was filtered off
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e8e2e31764804516ae76d234c7fed6cb
Source dataset
uspto-grants-1989_12
Patent number
US04888356

Reaction notes

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