Cyclopropanecarboxylic acid, 2-(3-methoxyphenyl)-, ethyl ester → 2-(3-Methoxyphenyl)cyclopropane-1-carboxylic acid

HRID 1994102

Reaction equation

HRID 1994102 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:11][CH:10]2[C:12]([O:14]CC)=[O:13])[CH:6]=[CH:7][CH:8]=1>[OH-].[Na+].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:11][CH:10]2[C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 19358490Cyclopropanecarboxylic acid, 2-(3-methoxyphenyl)-, ethyl ester

Product 1

HCID 139722332-(3-Methoxyphenyl)cyclopropane-1-carboxylic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 2-(3-methoxyphenyl)cyclopropanecarboxylate (1.63 g, 7.4 mmol) in 3N NaOH (35 mL) and MeOH (35 mL) was heated at 60° C. for 1 h. After cooling to rt, the reaction mixture was concentrated. The residue was dissolved in 1N HCl and extracted with DCM. The organic solutions were dried over Na2SO4, filtered, and concentrated to give the desired product (1.23 g, 87%) which was used without further fication. The cis and trans isomers were separated at a later stage of analog synthesis. LCMS: (FA) ES− 191.3 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in 1N HCl
  3. extractionextracted with DCM
  4. dry with materialThe organic solutions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-41cfcb53f06548289bd2b47e243398fd
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Linked notes

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