Carbon Dioxide → HCID 14817096, compound

HRID 1654432Notes

Reaction equation

HRID 1654432 reaction equation
C([Li])CCC.[CH:6]1([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=2[F:23])[CH2:8][CH2:7]1.[C:24](=[O:26])=[O:25]>C1COCC1>[CH:6]1([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:24]([OH:26])=[O:25])=[C:18]([F:22])[C:17]=2[F:23])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 14817095HCID 14817095, compoundHCID 178418339Butyllithium

Product 1

HCID 14817096HCID 14817096, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 ml of butyllithium (1.6M in hexane) were added dropwise at -60° C. to a solution of 11.7 g of 6-cyclopropylhexyloxy-2,3-difluorobenzene in 70 ml of THF. After 5 hours at -60° C., CO2 was passed in until saturation was complete. The solution was warmed to RT, the solvent was removed by distillation, 400 ml of H2O were added, and the mixture was acidified to pH 3 using acetic acid. The precipitate was filtered off with suction. 12.3 g of 4-(6-cyclopropylhexyloxy)-2,3-difluorobenzoic acid were obtained. Melting point 100°-108° C.

Workup

  1. customthe solvent was removed by distillation, 400 ml of H2O
  2. additionwere added
  3. filtrationThe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-df5365e59e6743cfb247f40ebcc8a6cf
Source dataset
uspto-grants-1995_04
Patent number
US05407599

Reaction notes

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