Hydrochloric Acid → HCID 178442528, compound

HRID 1154078Notes

Reaction equation

HRID 1154078 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C1(C)C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>C(O)C.[Ni].CO>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 516892Sodium BicarbonateHCID 18377907HCID 18377907, compound

Product 1

HCID 178442528HCID 178442528, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

4-(4'-heptylphenyl)phenol (200 g) is dissolved in ethanol (0.5 l) and a commercially available Raney nickel (20 g) is added, followed by hydrogenation in an autoclave at 80°to 120° C. under a hydrogen pressure of 30 to 40 Kg/cm2G. The reaction is traced by gas chromatography (column: SIDC-560-10%, 2 m, 280° C.) and is stopped when the raw material is extinct. The catalyst is filtered off from the hydrogenation product and ethanol is distilled off under reduced pressure, followed by dissolving the residue in toluene (200 ml). On the other hand, metallic sodium (18.4 g) is added to toluene (400 ml) and heated to 110° C., followed by quenching under a high speed agitation to prepare a sodium dispersion, which is then cooled down to room temperature, after which the above toluene solution of the hydrogenation product is added and the mixture is then agitated at room temperature for one hour. The resulting material is agitated at 100° C., for 4 hours, followed by cooling and then gradually adding methanol (200 ml). The whole is transferred into a separating funnel, followed by washings twice with 10% hydrochloric acid (200 ml) and once with a saturated aqueous solution of sodium hydrogen carbonate (200 ml) and repeated washings with water untill the water layer becomes neutral. The toluene layer is dried over anhydrous sodium sulfate, followed by distilling off toluene under reduced pressure, adding n-hexane (200 ml) and standing overnight to obtain crystals of trans-4-(4'-heptylphenyl)cyclohexanol. Yield: 41.6 g, 20.4%. M.p.: 80.2°-82.5° C.

Workup

  1. customfollowed by hydrogenation in an autoclave at 80°to 120° C. under a hydrogen
  2. customis traced by gas chromatography (column: SIDC-560-10%, 2 m, 280° C.)
  3. filtrationThe catalyst is filtered off from the hydrogenation product and ethanol
  4. distillationis distilled off under reduced pressure
  5. dissolutionby dissolving the residue in toluene (200 ml)
  6. additionOn the other hand, metallic sodium (18.4 g) is added to toluene (400 ml)
  7. customby quenching under a high speed agitation
  8. customto prepare a sodium dispersion, which
  9. temperatureis then cooled down to room temperature
  10. stirringThe resulting material is agitated at 100° C., for 4 hours
  11. temperatureby cooling
  12. customThe whole is transferred into a separating funnel
  13. washwashings with water untill the water layer
  14. dry with materialThe toluene layer is dried over anhydrous sodium sulfate
  15. distillationby distilling off toluene under reduced pressure
  16. additionadding n-hexane (200 ml)
  17. waitstanding overnight

Sources & evidence

ORD record
ord-ba7b3f906b4d45c3b30a80c988aa3f09
Source dataset
uspto-grants-1984_12
Patent number
US04487954

Reaction notes

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