Carbon Dioxide → 3-Cyclopropylbenzoic acid

HRID 732022

Reaction equation

HRID 732022 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH2:15][CH2:14]2)[CH:8]=1.[C:16](=[O:18])=[O:17]>>[CH:13]1([C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:16]([OH:18])=[O:17])[CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 32826721-Bromo-3-cyclopropylbenzeneHCID 178418339Butyllithium

Product 1

HCID 2820653-Cyclopropylbenzoic acid

Procedure

1.6 M n-Butyllithium in hexanes (3.2 mL, 5.1 mmol) was added drop-wise to a solution of 1-bromo-3-cyclopropyl-benzene at −78° C. and stirred for 1 hour. This reaction mixture was then transferred via canula to a 250 mL round bottom flask equipped with a stirrer bar approximately ¼ full of solid carbon dioxide and stirred and for 1 hour. The reaction mixture was concentrated and then the residue was diluted with water. The aqueous layer was washed with dichloromethane (3×), acidified with 1 N HCl to pH˜2, and extracted with ethyl acetate. The organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 3-cyclopropyl-benzoic (356 mg, 43%, white solid).

Workup

  1. customThis reaction mixture was then transferred via canula to a 250 mL round bottom flask
  2. stirringstirred and for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with water
  5. washThe aqueous layer was washed with dichloromethane (3×)
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with water and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford 3-cyclopropyl-benzoic (356 mg, 43%, white solid)

Sources & evidence

ORD record
ord-2b2875ec77e54f688239d75101e02be0
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Linked notes

Loading…