Hydrochloric Acid → HCID 59609849, compound

HRID 1929251Notes

Reaction equation

HRID 1929251 reaction equation
[Mg].[F:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[CH:7][CH:8]=1.[CH2:10]([CH:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl>C1COCC1.C(OCC)(=O)C>[CH2:10]([CH:17]1[CH2:18][CH2:19][C:20]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=2)([OH:23])[CH2:21][CH2:22]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 140821-Bromo-3-fluorobenzeneHCID 5462224MagnesiumHCID 131304504-Heptylcyclohexan-1-one

Product 1

HCID 59609849HCID 59609849, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Well-dried magnesium (8.3 g) and THF (20 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated to 50° C. 3-Fluorobromobenzene (8) (60.0 g) dissolved in THF (300 ml) was slowly added dropwise thereto in the temperature range of 40° C. to 60° C., and the mixture was stirred for another 60 minutes. Then, 4-heptylcyclohexanone (9) (50.0 g) dissolved in THF (150 ml) was slowly added dropwise thereto in the temperature range of 50° C. to 60° C., and the mixture was stirred for another 60 minutes. The reaction mixture obtained was cooled to 30° C., and then poured into a vessel containing an aqueous 1N—HCl solution (900 ml) and ethyl acetate (500 ml), and mixed. The mixture was then 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. The solvent was distilled off under reduced pressure, giving 80.0 g of 4-heptyl-1-(3-fluorophenyl)-cyclohexanol (10). The compound (10) obtained was a yellow oil.

Workup

  1. additionwas slowly added dropwise
  2. additionwas slowly added dropwise
  3. stirringin the temperature range of 50° C. to 60° C., and the mixture was stirred for another 60 minutes
  4. customThe reaction mixture obtained
  5. temperaturewas cooled to 30° C.
  6. additionpoured into a vessel
  7. additionmixed
  8. customhad separated into two phases of organic and aqueous phases
  9. customThe organic phase obtained
  10. washwashed with water
  11. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate
  12. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-79bc31ab1b6f4002b5ccdb7e57199158
Source dataset
uspto-grants-2012_05
Patent number
US08187494B2

Reaction notes

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