Acetic Acid → 1,3-Benzodioxole, 5-methoxy-

HRID 1602904Notes

Reaction equation

HRID 1602904 reaction equation
C(OC(C(C[C:11]1[CH:16]=[CH:15][C:14]2[O:17][CH2:18][O:19][C:13]=2[CH:12]=1)C(O)=O)=O)C.N1CCCCC1.[C:26](O)(=[O:28])C>C1C=CC=CC=1>[CH3:26][O:28][C:11]1[CH:16]=[CH:15][C:14]2[O:17][CH2:18][O:19][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8082PiperidineHCID 22131251HCID 22131251, compound

Product 1

HCID 5924531,3-Benzodioxole, 5-methoxy-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of the aldehyde of Example 1(p), (1.48 g, 5.25 mmol), 2-ethoxycarbonyl-3-(3,4-methylenedioxyphenyl)propanoic acid (2.34 g. 7.88 mmol), piperidine (223 mg, 0.26 ml, 2.7 mmol) and acetic acid (0. 17 ml) in benzene (50 ml) was stirred at reflux under argon using a Dean-Stark trap. After 18 hours, the benzene was removed in vacuo and the residue partitioned between t-butyl methyl ether and water. The layers were separated, and the aqueous further extracted (×3). The combined organic extracts were washed twice with water, 5% sodium bicarbonate solution, sat'd ammonium chloride, and brine, then dried (MgSO4), filtered and concentrated under reduced pressure. Silica gel chromatography (50% ether/hexanes) afforded the title compound as an oil. (1.048 g, 42%)

Workup

  1. temperatureat reflux under argon using a Dean-Stark trap
  2. customthe benzene was removed in vacuo
  3. customthe residue partitioned between t-butyl methyl ether and water
  4. customThe layers were separated
  5. extractionthe aqueous further extracted (×3)
  6. washThe combined organic extracts were washed twice with water, 5% sodium bicarbonate solution
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7d006bdc4d94ac38679b27836cf60f1
Source dataset
uspto-grants-1999_11
Patent number
US05985886

Reaction notes

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