Water → Naphthalene, 1,2-dihydro-4-(4-methoxyphenyl)-

HRID 485407Notes

Reaction equation

HRID 485407 reaction equation
O[C:2]1([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][CH2:4][CH:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13408689HCID 13408689, compound

Product 1

HCID 12048655Naphthalene, 1,2-dihydro-4-(4-methoxyphenyl)-Yield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-hydroxy-1-(4-methoxyphenyl)tetralin (18 g., 0.071 mole) in toluene (250 ml.) was treated with para-toluenesulfonic acid (5 mg.) and the resulting solution stirred at reflux for 16 hours, with complete water removal accomplished by means of a Dean-Stark trap. The reaction mixture was then cooled to room temperature, washed sequentially with 10% aqueous sodium bicarbonate solution (100 ml.), water (100 ml.) and saturated aqueous sodium chloride solution (100 ml.), dried (MgSO4) and evaporated under vacuum to an oil, which was purified by silica gel chromatography (elution with a hexane-toluene gradient) to give 12 g. of the named compound (67% yield, oil).

Workup

  1. washwashed sequentially with 10% aqueous sodium bicarbonate solution (100 ml.), water (100 ml.) and saturated aqueous sodium chloride solution (100 ml.)
  2. dry with materialdried (MgSO4)
  3. customevaporated under vacuum to an oil, which
  4. customwas purified by silica gel chromatography (
  5. washelution with a hexane-toluene gradient)
  6. customto give 12 g

Sources & evidence

ORD record
ord-14565c518550439888aa96d66f13e3a2
Source dataset
uspto-grants-1985_08
Patent number
US04536518

Reaction notes

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