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

HRID 865549Notes

Reaction equation

HRID 865549 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]

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 acid

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.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3199e72a622e4fb095f6eed15966f876
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

Loading…