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Hydrochloric Acid → Methyl alpha-(2-n-propyl-4-cyanophenoxy)-3,4-methylenedioxyphenylacetic acid

HRID 1378878
Notes
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Reaction equation

HRID 1378878 reaction equation
[CH2:1]([C:4]1[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][C:5]=1[O:6][CH:7]([C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)[C:8]([O:10]C)=[O:9])[CH2:2][CH3:3].[OH-].[Na+].[CH:29](Cl)(Cl)Cl.CO.[OH-].[NH4+].Cl>CO>[CH3:29][C:7]([C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)([O:6][C:5]1[CH:21]=[CH:22][C:23]([C:25]#[N:26])=[CH:24][C:4]=1[CH2:1][CH2:2][CH3:3])[C:8]([OH:10])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21873181Chloroform methanol ammonium hydroxideHCID 22912470Methyl alpha-(2-n-propyl-4-cyanophenoxy)-3,4-methylenedioxyphenylacetate

Product 1

HCID 22912495Methyl alpha-(2-n-propyl-4-cyanophenoxy)-3,4-methylenedioxyphenylacetic acidYield 99%

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

Procedure

To a solution of 3.5 g (8.64 mmol) of the product of Step C in 30 mL of methanol was added 2.07 mL (10.37 mmol) of 5.0N aqueous sodium hydroxide solution. After stirring overnight, TLC analysis (80:15:1 chloroform/methanol/ammonium hydroxide) indicated that the saponification was complete. The reaction mixture was acidified to pH 3 with 6N aqueous HCl and concentrated in vacuo. With heating and sonnication, the residue was redissolved in ethyl acetate, washed with brine, dried over magnesium sulfate, filtered, and the filtrate evaporated in vacuo to afford 2.92 g (99%) of the title compound as an amorphous solid which was used without further purification in the next step.

Workup

  1. concentrationconcentrated in vacuo
  2. temperatureWith heating
  3. dissolutionsonnication, the residue was redissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-01accdfc58ea48678b7ece76143b84a6
Source dataset
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05668176

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes