Hydroquinone → 4-Methoxybicyclo[2.2.2]octan-2-one

HRID 66087

Reaction equation

HRID 66087 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O.[C:20]([CH:23]1[CH2:28][CH2:27][C:26]([O:29][CH3:30])=[CH:25][CH2:24]1)(=[O:22])[CH3:21].C[O-].[Na+].CC(=O)CCCCCC>C1C=CC=CC=1.O>[CH3:30][O:29][C:26]12[CH2:27][CH2:28][CH:23]([CH2:24][CH2:25]1)[C:20](=[O:22])[CH2:21]2

Participants

8

Reactant 5

HCID 785HydroquinoneHCID 6101p-Toluenesulfonic acidHCID 80932-OctanoneHCID 10942334Sodium MethoxideHCID 203422181-Acetyl-4-methoxy-3-cyclohexene

Product 1

HCID 5663034-Methoxybicyclo[2.2.2]octan-2-one

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 13.2 g. of p-toluenesulfonic acid and 0.9 g. of hydroquinone in 540 ml. of benzene was heated at reflux under a Dean Stark trap until no more water was evolved. A solution of 90.6 g. of 1-Acetyl-4-methoxy-3-cyclohexene in 750 ml. of benzene was then added to the refluxing soltuion over 6 hrs. Following an additional hr's heating the mixture was cooled and treated with 16 ml. of 4.64N methanolic sodium methoxide. The mixture was washed twice with water and the solvent evaporated in vacuum. The residual oil was distilled at 0.45 mm to afford 64.2 g. of bicyclic ketone 4-Methoxybicyclo[2,2,2].octan-2-one, bp 77°-82°.

Workup

  1. additionA mixture of 13.2 g
  2. temperatureheating the mixture
  3. temperaturewas cooled
  4. additiontreated with 16 ml
  5. washThe mixture was washed twice with water
  6. customthe solvent evaporated in vacuum
  7. distillationThe residual oil was distilled at 0.45 mm
  8. customto afford 64.2 g

Sources & evidence

ORD record
ord-f24876691f96463194109662804a3f0c
Source dataset
uspto-grants-1978_12
Patent number
US04130561

Linked notes

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