Sodium Hydroxide → HCID 54057846, compound

HRID 1756763Notes

Reaction equation

HRID 1756763 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([CH2:11][CH:12]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]2[O:24][CH2:25][O:26][C:19]=12)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])C(OCC)=O)C.[OH-].[Na+]>C(O)C>[CH2:25]1[O:24][C:20]2[C:19](=[C:18]([CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][CH2:5][C:4]([OH:27])=[O:3])[CH:23]=[CH:22][CH:21]=2)[O:26]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67786251HCID 67786251, compound

Product 1

HCID 54057846HCID 54057846, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.49 g (3.94 mmol) of 2-(2, 3-methylenedioxyphenyl)heptylmalonic acid diethylester in 10 ml of ethanol was added 6.6 g of 10% aqueous sodium hydroxide, and the resultant mixture was refluxed under heating for 2.5 hours. The reaction mixture was concentrated in vacuo, mixed with 5 ml of water and 0.8 ml of conc. sulfuric acid and refluxed under heating for 4 hours. After cooling, the reaction mixture was shaken with ethyl acetate, and the extract was washed with saturated saline, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane (1/2) to give 0.92 g of 4-(2, 3-methylenedioxyphenyl) nonanoic acid as an oil.

Workup

  1. temperatureunder heating for 2.5 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionmixed with 5 ml of water and 0.8 ml of conc. sulfuric acid
  4. temperaturerefluxed
  5. temperatureunder heating for 4 hours
  6. temperatureAfter cooling
  7. washthe extract was washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent evaporated
  10. customThe residue was chromatographed on a silica gel column
  11. washeluting with ethyl acetate/hexane (1/2)

Sources & evidence

ORD record
ord-156170dd442a411dab153a8060659486
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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