Acetone → Ethyl alpha-(4-carbomethoxy-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetate

HRID 865541Notes

Reaction equation

HRID 865541 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH2:13][CH3:14].Br[CH:16]([C:22]1[CH:27]=[CH:26][C:25]2[O:28][CH2:29][O:30][C:24]=2[CH:23]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>CCOCC>[C:6]([C:5]1[CH:10]=[CH:11][C:2]([O:1][CH:16]([C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:3]([CH2:12][CH2:13][CH3:14])[CH:4]=1)([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 11805593Methyl 4-hydroxy-3-propylbenzoateHCID 15383768Ethyl alpha-bromo-3,4-methylenedioxyphenylacetate

Product 1

HCID 15383769Ethyl alpha-(4-carbomethoxy-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a nitrogen flushed 5 L three neck round bottom flask fitted with a mechanical stirrer, condenser, and a nitrogen inlet was charged 326 g (1.68 mol) of methyl 4-hydoxy-3-n-propylbenzoate, 507.6 g (1.73 mol)of ethyl α-bromo-3,4-methylenedioxyphenylacetate from above, 235 g (1.70 mol) of anhydrous potassium carbonate, and 1.7 L of acetone. The mixture was refluxed with vigorous stirring for 9 hr. The suspension was allowed to cool to ambient temperature and stirred overnight. The mixture diluted with 2 L of ether, cooled to 0° C. and filtered through Super-CelR. The cake washed with ether and the combined filtrate concentrated. The residue was redissolved in ether and the organic layer washed with once with 1 N HCl, saturated sodiuim bicarbonate solution, 10% sodium bisulfite solution, brine, dried with magnesium sulfate, treated with charcoal and filtered through a plug of silica. The pale yellow solution was concentrated to 697.3 g (theoretical 678 g) of a thick yellow oil which was used without purification in the next step. NMR was consistent with the title compound.

Workup

  1. customTo a nitrogen flushed 5 L three neck round bottom flask
  2. customfitted with a mechanical stirrer, condenser, and a nitrogen inlet
  3. temperatureThe mixture was refluxed
  4. stirringstirred overnight
  5. temperaturecooled to 0° C.
  6. filtrationfiltered through Super-CelR
  7. washThe cake washed with ether
  8. concentrationthe combined filtrate concentrated
  9. dissolutionThe residue was redissolved in ether
  10. washthe organic layer washed with once with 1 N HCl, saturated sodiuim bicarbonate solution, 10% sodium bisulfite solution, brine
  11. dry with materialdried with magnesium sulfate
  12. additiontreated with charcoal
  13. filtrationfiltered through a plug of silica
  14. concentrationThe pale yellow solution was concentrated to 697.3 g (theoretical 678 g) of a thick yellow oil which
  15. customwas used without purification in the next step

Sources & evidence

ORD record
ord-c2127c732fb547df89098b375a6c2ed8
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

Loading…