Hydrochloric Acid → alpha-(4-Acetyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetic acid

HRID 964471Notes

Reaction equation

HRID 964471 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:10]([O:12]C)=[O:11])=[C:6]([CH2:25][CH2:26][CH3:27])[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].C(Cl)(Cl)Cl.CO.[NH4+].[OH-].Cl>CO>[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:10]([OH:12])=[O:11])=[C:6]([CH2:25][CH2:26][CH3:27])[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19080436Methyl alpha-(4-acetyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetateHCID 21873181Chloroform methanol ammonium hydroxide

Product 1

HCID 19080456alpha-(4-Acetyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.556 g (1.50 mmol) of the product of Step B dissolved in 4.0 mL of methanol was added 0.45 mL (2.25 mmol) of a 5.0N aqueous solution of sodium hydroxide. The reaction mixture was stirred at room temperature and monitored by TLC (CHCl3 --MeOH--NH4OH 80:15:1). After 4 hours the reaction was judged to be complete and the reaction mixture was adjusted to pH=7 with 6.0N HCl. The mixture was then evaporated in vacuo and the residue was purified on a silica gel flash chromatography column eluted with CHCl3 --MeOH--NH4OH (80:15:1). Evaporation of the purified fractions and drying in vacuo afforded 0.416 g (78%) of the title compound.

Workup

  1. customThe mixture was then evaporated in vacuo
  2. customthe residue was purified on a silica gel flash chromatography column
  3. washeluted with CHCl3 --MeOH--NH4OH (80:15:1)
  4. customEvaporation of the purified fractions
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-be4945b83aab4ac88706b4cf77d86d17
Source dataset
uspto-grants-1998_06
Patent number
US05767310

Reaction notes

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