Benzene → HCID 19009062, compound

HRID 1742220Notes

Reaction equation

HRID 1742220 reaction equation
[CH2:1]([NH:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([OH:16])[CH:10]=1)[CH2:2][CH2:3][CH3:4].[CH:18]1[CH:23]=CC=C[CH:19]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([NH:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][C:18]([CH3:23])([CH3:19])[O:16][C:11]=2[CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 15132212HCID 15132212, compound

Product 1

HCID 19009062HCID 19009062, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of N-butyl-3-(3,4- dihydroxyphenyl)propionamide was dissolved in a mixed solvent consisting of 30 ml of benzene and 10 ml of tetrahydrofuran and 4 ml of acetonedimethylacetal was added to the solution. Then a small amount of p-toluenesulfonic acid was added to the solution and the solution was stirred for 11 hours under reflux. With a further addition of 2 ml of acetonedimethyl acetal, stirring was continued under reflux for 6 hours. After cooling, the solution was poured over ice water containing sodium hydrogen carbonate and was mixed thoroughly. The solution was extracted with ethyl acetate, washed with water and then dried with sodium sulfate anhydride. After removing the solvent by evaporation under reduced pressure, the resulting residue was purified by chromatography on silica gel column using a mixed solvent (chloroform:methanol=100:l) and thus 0.84 g of oily N-butyl-3-(2,2-dimethyl-1,3-benzodioxol-5-yl)propionamide was obtained.

Workup

  1. additionwas added to the solution
  2. temperatureunder reflux
  3. stirringstirring
  4. temperatureunder reflux for 6 hours
  5. temperatureAfter cooling
  6. additionwas mixed thoroughly
  7. extractionThe solution was extracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried with sodium sulfate anhydride
  10. customAfter removing the solvent
  11. customby evaporation under reduced pressure
  12. customthe resulting residue was purified by chromatography on silica gel column

Sources & evidence

ORD record
ord-363faeb606234f099970f5282a1eef3d
Source dataset
uspto-grants-1994_08
Patent number
US05338745

Reaction notes

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