Hydrochloric Acid → HCID 59609814, compound

HRID 1929262Notes

Reaction equation

HRID 1929262 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 (42) (57 g) and THF (100 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 ml) was added dropwise thereto in the temperature range of −74° C. to −70° C., and the mixture was stirred for another 2 hours. Subsequently, 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 mixture was stirred for 8 hours while allowing the temperature to come to 25° C. The reaction mixture obtained was added into a vessel containing an aqueous 1N—HCl solution (500 ml) and ethyl acetate (500 ml), and mixed. Subsequently, the mixture was allowed to stand until it had separated into two phases of organic and aqueous phases, and an extractive operation was carried out. The organic phase obtained was fractionated, washed 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 (47). The compound (47) obtained was a yellow oily material.

Workup

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

Sources & evidence

ORD record
ord-ab37887276184dcb86680d059789536f
Source dataset
uspto-grants-2012_05
Patent number
US08187494B2

Reaction notes

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