6-Methoxy-1,2,3,4-tetrahydronaphthalen-1-ol → 7-Methoxy-1,2-dihydronaphthalene

HRID 606356

Reaction equation

HRID 606356 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9](O)[CH2:8][CH2:7][CH2:6]2>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10]([CH:9]=[CH:8][CH2:7][CH2:6]2)=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 110522116-Methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 5947787-Methoxy-1,2-dihydronaphthaleneYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

Crude 6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol (10.3 g, 0.058 mol) was dissolved in 100 ml of toluene and heated in an oil bath (115° C.). P-tolylsulphonic acid (20 mg) was added to the reaction mixture and it was refluxed for about 1 h. The reaction was monitored by GC. The reaction mixture was then cooled and washed with sat. NaHCO3 solution, water and brine and organic layer was dried over Na2SO4. Concentration gave 8.879 of light brown oil. Yield 96%.

Workup

  1. temperaturewas refluxed for about 1 h
  2. temperatureThe reaction mixture was then cooled
  3. washwashed with sat. NaHCO3 solution, water and brine and organic layer
  4. dry with materialwas dried over Na2SO4
  5. concentrationConcentration
  6. customgave 8.879 of light brown oil

Sources & evidence

ORD record
ord-22b350368a154bf89a87ab4c815cb4f1
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Linked notes

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