Potassium Carbonate → HCID 10654815, compound

HRID 1954219Notes

Reaction equation

HRID 1954219 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:4]([CH:5]=O)[C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:20]C(OCC)CBr)[CH3:19].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(O)(=O)C.CCOCC>[CH3:10][C:7]1[C:4]2[CH:5]=[C:19]([CH:18]=[O:20])[O:11][C:3]=2[C:2]([CH3:1])=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium BicarbonateHCID 8192973,6-Dimethylsalicylaldehyde

Product 1

HCID 10654815HCID 10654815, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To 200 ml of a solution of 17.4 g of 3,6-dimethylsalicylaldehyde in N,N-dimethyformamide were added 32 g of anhydrous potassium carbonate and 17.8 ml of bromoacetaldehyde diethyl acetal. The resulting mixture was stirred at 150° C. for 2.5 hours, cooled to room temperature by allowing to stand, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to give 23.4 g of an ether. This ether was dissolved in 120 ml of acetic acid. The resulting solution was refluxed under nitrogen stream for 8 hours, cooled to room temperature by allowing to stand, and poured into a saturated aqueous solution of sodium bicarbonate. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting crude product was washed with hexane to give 7.8 g of the title compound as a pale yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe resulting residue was purified by silica gel column chromatography
  7. customto give 23.4 g of an ether
  8. temperatureThe resulting solution was refluxed under nitrogen stream for 8 hours
  9. temperaturecooled to room temperature
  10. extractionThe resulting mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was evaporated
  14. washThe resulting crude product was washed with hexane

Sources & evidence

ORD record
ord-c57ad88b9fc146f7b6348b8483a20985
Source dataset
uspto-grants-2000_09
Patent number
US06121309

Reaction notes

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