Potassium Hydroxide → Bis-(3,4-methylenedioxyphenylmethyl)acetic acid

HRID 976041Notes

Reaction equation

HRID 976041 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]4[O:27][CH2:28][O:29][C:23]=4[CH:22]=3)(C(OC)=O)[C:12]([O:14]C)=[O:13])=[CH:4][C:3]=2[O:2]1.[OH-].[K+]>C(O)CCC.O>[CH2:28]1[O:27][C:24]2[CH:25]=[CH:26][C:21]([CH2:20][CH:11]([CH2:10][C:5]3[CH:6]=[CH:7][C:8]4[O:9][CH2:1][O:2][C:3]=4[CH:4]=3)[C:12]([OH:14])=[O:13])=[CH:22][C:23]=2[O:29]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19968591Dimethyl bis-(3,4-methylenedioxyphenylmethyl)-malonate

Product 1

HCID 19968575Bis-(3,4-methylenedioxyphenylmethyl)acetic acidYield 55.2%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A solution of 20.58 g (0.051 mol) of dimethyl bis-(3,4-methylenedioxyphenylmethyl)malonate in 50 mL of n-butanol was treated with a solution of 8.58 g (0.153 mol) of KOH in 50 mL H2O and heated at reflux overnight. The solvent was removed under reduced pressure and the residue mixed with H2O and acidified to pH 2 with dilute HCl. The mixture was extracted with EtOAc and the EtOAc washed with saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 9.24 g (55% yield) of the product as a solid, mp 191°-193° C. The structure was confirmed by NMR spectroscopy.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue mixed with H2O
  5. extractionThe mixture was extracted with EtOAc
  6. washthe EtOAc washed with saturated NaCl
  7. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-cadd359018844974b964224c6c6fa38b
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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