Ethanol → trans-3-(3-Methoxy-phenyl)-2,2-dimethyl-cyclopropanecarboxylic acid

HRID 2240854Notes

Reaction equation

HRID 2240854 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[C:7]1([CH3:18])[CH3:17])=[O:5])C.CCO.[OH-].[Na+]>O>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([C@H:8]2[C@H:6]([C:4]([OH:5])=[O:3])[C:7]2([CH3:18])[CH3:17])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 57652816trans-3-(3-Methoxy-phenyl)-2,2-dimethyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 57652758trans-3-(3-Methoxy-phenyl)-2,2-dimethyl-cyclopropanecarboxylic acidYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trans-3-(3-Methoxy-phenyl)-2,2-dimethyl-cyclopropanecarboxylic acid ethyl ester (15.22 g, 61 mmol) was added to a mixture of EtOH (200 mL) and 2M aqueous NaOH (100 mL). Solid NaOH (5.0 g, 125 mmol) was added, and the reaction mixture was stirred under N2 atmosphere for 15 hours at room temperature. The reaction mixture was diluted with water and extracted twice with a mixture of 1/1 hexanes/diethyl ether and once with EtOAc. The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure to give 11.5 g of trans-3-(3-methoxy-phenyl)-2,2-dimethyl-cyclopropanecarboxylic acid, MS=221 [M+H]+.

Workup

  1. extractionextracted twice with a mixture of 1/1 hexanes/diethyl ether and once with EtOAc
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-641a8e97990c465c9b8283538c0b5ddd
Source dataset
uspto-grants-2010_05
Patent number
US07723391B2

Reaction notes

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