Hydrochloric Acid → 2-[2-(4-Methoxyphenyl)cyclopropyl]acetic acid

HRID 1909537Notes

Reaction equation

HRID 1909537 reaction equation
CON(C)[C:4](=[O:17])[CH2:5][CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[OH-:19].[Na+].Cl>CCO>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH:7]2[CH2:8][CH:6]2[CH2:5][C:4]([OH:17])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22347607N-methoxy-2-(2-(4-methoxyphenyl)cyclopropyl)-N-methylacetamide

Product 1

HCID 223476082-[2-(4-Methoxyphenyl)cyclopropyl]acetic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of N-methoxy-2-(2-(4-methoxyphenyl)cyclopropyl)-N-methylacetamide (559) (1.8 g, 7.4 mmol), 2.5N NaOH (15 mL) and EtOH (15 mL) was stirred at 60° C. for 24 hours. The reaction mixture was acidified with HCl and extracted with EtOAc. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo to provide 2-(2-(4-methoxyphenyl)cyclopropyl)acetic acid (560) (1.5 g, 96.1%) as a yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81ea7d9b4f6f46018b841809cedbbe11
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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