7-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one → 7-hydroxy-3,4-dihydro-2H-naphthalen-1-one

HRID 449523Notes

Reaction equation

HRID 449523 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1>Br>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-oneYield 110.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
100 °C

Procedure

The 7-methoxy-1-tetralone (Aldrich, Cat. #163368) (0.75 g, 4.2 mmol) was dissolved in conc hydrobromic acid (3.0 ml) and was heated to 100° C. for 8 h. The reaction was allowed to cool to r.t. and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give crude 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one (0.75 g, 100%) as a semisolid.Analytical LCMS (M+H)+: m/z=163.0.

Workup

  1. temperatureto cool to r.t.
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5781a811b9a241eba7f645fc8d267a21
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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