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

HRID 744186Notes

Reaction equation

HRID 744186 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-Cel®. The cake washed with ether and the combined filtrate concentrated. The residue was redissolved in ether and the organic layer washed with once with 1N 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 7.3 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-Cel®
  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 1N 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 7.3 g (theoretical 678 g) of a thick yellow oil which
  15. customwas used without purification in the next step

Sources & evidence

ORD record
ord-787c87b1c2f145fca4711d2d63dad69c
Source dataset
uspto-grants-1996_09
Patent number
US05559135

Reaction notes

Loading…