Carbon Dioxide → 2,6-Difluoro-4-pentylbenzoic acid

HRID 466494Notes

Reaction equation

HRID 466494 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:10]=[C:11]([F:13])[CH:12]=1.[C:19](=[O:21])=[O:20].CCOCC>C1COCC1>[F:6][C:7]1[CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:10]=[C:11]([F:13])[C:12]=1[C:19]([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 157519781,3-Difluoro-5-pentylbenzeneHCID 178418339Butyllithium

Product 1

HCID 190101792,6-Difluoro-4-pentylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium (10.5M in hexane; 2.70 ml, 0.028 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 13 (5.10 g, 0.028 mol) in dry THF (30 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and then poured onto a slurry of solid carbon dioxide and dry ether. The product was extracted into 10% sodium hydroxide which was then acidified with 36% hydrochloric acid. The acidic mixture was washed with ether (twice), and the combined ethereal layers were washed with water and dried (MgSO4). The solvent was removed in vacuo to yield a colourless solid.

Workup

  1. temperatureThe stirred mixture was maintained under these conditions for 2.5 h
  2. extractionThe product was extracted into 10% sodium hydroxide which
  3. washThe acidic mixture was washed with ether (twice), and the combined ethereal layers
  4. washwere washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customto yield a colourless solid

Sources & evidence

ORD record
ord-eecfd88f3d4945319632e1940c5c7162
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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