Hydrochloric Acid → 4-(4-Butoxy-2,3-difluorophenyl)-4'-propylbicyclohexyl-4-ol

HRID 2220576Notes

Reaction equation

HRID 2220576 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[F:13])[CH2:2][CH2:3][CH3:4].[Li]CCCC.[CH2:19]([CH:22]1[CH2:27][CH2:26][CH:25]([CH:28]2[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]2)[CH2:24][CH2:23]1)[CH2:20][CH3:21].Cl>C1COCC1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:31]2([OH:34])[CH2:30][CH2:29][CH:28]([CH:25]3[CH2:26][CH2:27][CH:22]([CH2:19][CH2:20][CH3:21])[CH2:23][CH2:24]3)[CH2:33][CH2:32]2)=[C:8]([F:12])[C:7]=1[F:13])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 27829391-Butoxy-2,3-DifluorobenzeneHCID 4354185[1,1'-Bicyclohexyl]-4-one,4'-propyl-,HCID 178418339Butyllithium

Product 1

HCID 589918854-(4-Butoxy-2,3-difluorophenyl)-4'-propylbicyclohexyl-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

31.0 g (0.17 mol) of 1-butoxy-2,3-difluorobenzene are initially introduced in 200 ml of THF, and 100 ml (0.16 mol) of n-BuLi (15% soln. in hexane) are added at −70° C. After 2 h at this temperature, a solution of 35.6 g (0.16 mol) of 4′-propylbicyclohexyl-4-one in 200 ml of THF is metered in, and the batch is stirred for 2.5 h. The reaction mixture is hydrolysed with ice-cooling and acidified using 2 N HCl. The solution is extracted with MTBE, and the combined organic phases are washed with sat. sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the crude product (66.3 g of yellow solid) is used directly for the following reaction.

Workup

  1. temperaturecooling
  2. extractionThe solution is extracted with MTBE
  3. washthe combined organic phases are washed with sat. sodium chloride solution
  4. customdried
  5. concentrationThe solution is concentrated to dryness
  6. customthe crude product (66.3 g of yellow solid) is used directly for the following reaction

Sources & evidence

ORD record
ord-16d624de9cda4318a0367a9c6529983c
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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