Phenol → HCID 22995028, compound

HRID 1168040Notes

Reaction equation

HRID 1168040 reaction equation
Cl[C:2]1([CH3:10])[CH2:7][CH2:6][C:5](Cl)([CH3:8])[CH2:4][CH2:3]1.[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:10][C:2]12[CH2:7][CH2:6][C:5]([CH3:8])([CH2:4][CH2:3]1)[C:14]1[CH:15]=[CH:16][C:11]([OH:17])=[CH:12][C:13]2=1

Participants

4

Reactant 3

HCID 996PhenolHCID 6451240Aluminum(III) ChlorideHCID 124109771,4-Dichloro-1,4-dimethylcyclohexane2×

Product 1

HCID 22995028HCID 22995028, compound

Conditions

Temperature
120 °C

Procedure

To a solution of 1,4-dichloro-1,4-dimethylcyclohexane (Compound 1, 3 g, 16.5 mmol) and phenol (1.55 g, 16.5 mmol) under argon at 25° C. was slowly added aluminum chloride (0.22g, 0.165 mmol). The resulting mixture was heated to 120° C. for 12 hours, and then it was quenched with ice. The products were extracted with CH2Cl2, the layers separated, and the organic layer was washed with water and brine. The organic layer was dried over Na2SO4, and filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate:hexane (1:9) to yield the title compound as a yellow oil.

Workup

  1. customat 25° C.
  2. customit was quenched with ice
  3. extractionThe products were extracted with CH2Cl2
  4. customthe layers separated
  5. washthe organic layer was washed with water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-47af6a6381c545718f2f1353aee59f23
Source dataset
uspto-grants-2003_09
Patent number
US06620963B1

Reaction notes

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