Hydrochloric Acid → HCID 57279758, compound

HRID 1584527Notes

Reaction equation

HRID 1584527 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Al].[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.Cl>O.C1(C)C(C)=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[C:9]([C:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73934-tert-ButylphenolHCID 7967CyclohexanoneHCID 5359268Aluminum

Product 1

HCID 57279758HCID 57279758, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

15.0 g (0.10 mol) of 4-tert-butylphenol and 7.2 g (0.035 mol) of aluminium isopropylate are added to 100 ml of xylene under nitrogen. To remove the resulting isopropanol, 30 ml of solvent are distilled off. The reaction mixture is heated to 100° C. and charged with 9.8 g (0.10 mol) of cyclohexanone and is then refluxed for 20 hours. The reaction mixture is cooled and charged with 40 ml of water and 10 ml of concentrated hydrochloric acid. The organic phase is separated, washed with water, dried over magnesium sulfate and concentrated on a rotary evaporator. The residue is chromatographed over silica gel using the solvent system hexane/ethyl acetate=19:1 and the pure fractions are crystallised from methanol, giving 6.3 g (27%) of 4-tert-butyl-2-cyclohexen-1-yl-phenol, m.p. 90-93° C. (compound (109), Table 1).

Workup

  1. customTo remove the resulting isopropanol, 30 ml of solvent
  2. distillationare distilled off
  3. temperatureis then refluxed for 20 hours
  4. temperatureThe reaction mixture is cooled
  5. customThe organic phase is separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated on a rotary evaporator
  9. customThe residue is chromatographed over silica gel using the solvent system hexane/ethyl acetate=19:1
  10. customthe pure fractions are crystallised from methanol

Sources & evidence

ORD record
ord-f2d9bdd9bd1746d496562a212a2208b3
Source dataset
uspto-grants-1999_08
Patent number
US05932642

Reaction notes

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