Potassium bisulfate → HCID 178447838, compound

HRID 1165111Notes

Reaction equation

HRID 1165111 reaction equation
S([O-])(O)(=O)=O.[K+].O[C:8]1([C:23]2[CH:24]=[C:25]([F:29])[CH:26]=[CH:27][CH:28]=2)[CH2:13][CH2:12][CH:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1>>[CH2:20]([C@H:17]1[CH2:16][CH2:15][C@H:14]([CH:11]2[CH2:12][CH2:13][C:8]([C:23]3[CH:24]=[C:25]([F:29])[CH:26]=[CH:27][CH:28]=3)=[CH:9][CH2:10]2)[CH2:19][CH2:18]1)[CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 516920Potassium bisulfateHCID 178447896HCID 178447896, compound

Product 1

HCID 178447838HCID 178447838, compound

Procedure

Slaked magnesium (4.8 g, 0.2 mol) was placed in a three-necked flask, followed by slowly dropwise adding a solution of 3-fluorobromobenzene (I) (35.0 g, 0.2 mol) dissolved in anhydrous tetrahydrofuran (50 ml) in nitrogen gas current with stirring while keeping the reaction temperature at 30°-35° C. to obtain a black-gray colored, uniform tetrahydrofuran solution of 3-fluorophenylmagnesium bromide (II), dropwise adding to this solution, a solution of 4-(trans-4-propylcyclohexyl)cyclohexanone (a compound of the formula (III) wherein R1 =C3H7) (46.7 g, 0.21 mol) dissolved in tetrahydrofuran (50 ml) over 30 minutes while keeping the reaction temperature at 5°-10° C., raising the temperature up to 35° C. after completion of the dropwise addition, aging the resulting solution for one hour, adding 3N hydrochloric acid (100 ml), extracting the resulting separated oily substance with toluene (100 ml) with stirring, washing the extract solution with water until the washing water became neutral to obtain a toluene solution of a 3-[1-hydroxy-4-(trans-4-propylcyclohexyl)cyclohexyl]fluorobenzene (a compound of the formula (IV) wherein R1 =C3H7), adding potassium hydrogen sulfate (3.2 g) to the toluene extract solution, removing the resulting water in the form of an azeotrope with toluene under reflux on heating, washing the toluene solution after completion of the reaction with water until the washing water became neutral, distilling off toluene to obtain a concentrated substance of 3-[4-(trans-4-propylcyclohexyl)cyclohexen -1-yl]fluorobenzene (a compound of the formula (V) wherein R1 =C3H7), dissolving this substance without purification in ethyl alcohol (200 ml), subjecting the solution to catalytic reduction reaction using a developed Raney Ni (2.0 g) as a catalyst under the atmospheric pressure and at 25° C., filtering off Raney Ni after hydrogen absorption has ceased, distilling off ethyl alcohol from the ethyl alcohol filtrate and recrystallizing the residue from ethyl acetate, to obtain 3-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]fluorobenzene (a compound of the formula (VI) wherein R1 =C3H7) . (38.7 g).

Workup

  1. extractionextract solution
  2. customremoving the resulting water in the form of an azeotrope with toluene
  3. temperatureunder reflux
  4. temperatureon heating
  5. washwashing the toluene solution
  6. customafter completion of the reaction with water until the washing water
  7. distillationdistilling off toluene

Sources & evidence

ORD record
ord-3dda6f0c2f854efab9ab6854cef44bf0
Source dataset
uspto-grants-1990_03
Patent number
US04908152

Reaction notes

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