Hydrochloric Acid → HCID 59609814, compound

HRID 1943548Notes

Reaction equation

HRID 1943548 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].C([Li])(CC)C.[CH2:14]([O:18][CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1)[CH2:15][CH2:16][CH3:17].Cl>C(OCC)(=O)C.C1COCC1.C1CCCCC1.CCCCCC>[CH2:14]([O:18][CH:19]1[CH2:20][CH2:21][C:22]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[F:8])([OH:25])[CH2:23][CH2:24]1)[CH2:15][CH2:16][CH3:17]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 97061,2-DifluorobenzeneHCID 184137274-Butoxycyclohexan-1-oneHCID 178418400CID 53628100

Product 1

HCID 59609814HCID 59609814, compoundYield 91.6%

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,2-Difluorobenzene (21) (57.0 g) and THF (1000 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to −74° C. sec-Butyllithium (1.00 M, in a n-hexane and cyclohexane solution; 500.0 ml) was added dropwise thereto in the temperature range of −74° C. to −70° C., and the mixture was stirred for another 2 hours. Then, 4-butoxycyclohexanone (22) (85.1 g) in a THF (200 ml) solution was added dropwise thereto in the temperature range of −75° C. to −70° C., and the stirring was continued for another 8 hours while the mixture was allowed to return to 25° C. The reaction mixture obtained was poured into a vessel containing an aqueous 1N-HCl solution (500 ml) and ethyl acetate (500 ml), and mixed. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed sequentially with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, giving 130.1 g of 4-butoxy-(2,3-difluorophenyl)cyclohexanol (23). The obtained compound (23) was a yellow oil.

Workup

  1. addition500.0 ml) was added dropwise
  2. waitin the temperature range of −75° C. to −70° C., and the stirring was continued for another 8 hours while the mixture
  3. customto return to 25° C
  4. customThe reaction mixture obtained
  5. additionwas poured into a vessel
  6. additionmixed
  7. customhad separated into organic and
  8. extractionaqueous phases, and extraction into an organic phase
  9. customThe organic phase obtained
  10. washwashed sequentially with water
  11. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate
  12. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7e48439367d9416daea7df5052a65234
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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