Sodium Hydroxide → 2-(3-Chlorophenyl)cyclopropanecarboxylic acid

HRID 2085071Notes

Reaction equation

HRID 2085071 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:7][C@H:6]1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)=[O:4].[OH-].[Na+]>CO>[Cl:14][C:10]1[CH:9]=[C:8]([CH:6]2[CH2:7][CH:5]2[C:3]([OH:4])=[O:2])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11183432Methyl (1R,2R)-2-(3-chlorophenyl)cyclopropane-1-carboxylate

Product 1

HCID 234230182-(3-Chlorophenyl)cyclopropanecarboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude cyclopropanated ester from above (1.09 g, 5.17 mmol) was dissolved in 30 mL MeOH and treated with 15 mL of 2 M aqueous NaOH solution. The mixture was stirred at room temperature for 2 h. It was then placed on a rotary evaporator to remove the MeOH. The remaining solution was diluted with water (30 mL), washed with ether (15 mL), then acidified with 5 M aqueous HCl solution. The product was extracted with ether (3×40 mL) and the combined organics were washed with brine and dried (MgSO4). After filtration, the solvents were removed in vacuo to afford 792 mg of 2-(3-chlorophenyl)-cyclopropanecarboxylic acid as a white solid (4.03 mmol, 78% yield).

Workup

  1. customIt was then placed on a rotary evaporator
  2. customto remove the MeOH
  3. additionThe remaining solution was diluted with water (30 mL)
  4. washwashed with ether (15 mL)
  5. extractionThe product was extracted with ether (3×40 mL)
  6. washthe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationAfter filtration
  9. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-f17b774645db46778359a70c96a145ab
Source dataset
uspto-grants-2004_04
Patent number
US06720321B2

Reaction notes

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