Carbon Dioxide → 4-(Butylthio)benzoic acid

HRID 1901392Notes

Reaction equation

HRID 1901392 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:8]=1.[C:18](=[O:20])=[O:19]>C1COCC1>[CH2:14]([S:13][C:10]1[CH:11]=[CH:12][C:7]([C:18]([OH:20])=[O:19])=[CH:8][CH:9]=1)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 14418074(4-Bromophenyl)(butyl)sulfaneHCID 178418339Butyllithium

Product 1

HCID 4217574-(Butylthio)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (6.8 ml, 10.0M in hexane, 0.068 mol) was added to a stirred, cooled (-78° C.) solution of compound 1 (16.56 g, 0.067 mol) in dry THF (200 ml), under dry nitrogen at -78° C. The mixture was maintained under these conditions for a further 0.5 h (glc analysis confirmed a complete reaction) before being poured into a slurry of `Cardice` and dry THF. The mixture was allowed to warm to room temperature overnight. The combined organic extracts were evaporated in vacuo and the residue was dissolved in boiling acetic acid. Ice (400 g) was added to the solution and the product was filtered off and dried in vacuo (KOH, P2O5).

Workup

  1. customat -78° C
  2. temperatureThe mixture was maintained under these conditions for a further 0.5 h (glc analysis
  3. customa complete reaction)
  4. customThe combined organic extracts were evaporated in vacuo
  5. dissolutionthe residue was dissolved
  6. additionIce (400 g) was added to the solution
  7. filtrationthe product was filtered off
  8. dry with materialdried in vacuo (KOH, P2O5)

Sources & evidence

ORD record
ord-aba6ea49d05f4bf882521f01963b8cf3
Source dataset
uspto-grants-1996_11
Patent number
US05578242

Reaction notes

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