6-Methoxy-alpha-tetralone → 6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

HRID 1456546Notes

Reaction equation

HRID 1456546 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2

Participants

3

Reactant 1

HCID 141126-Methoxy-alpha-tetralone

Product 1

HCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneYield 93.6%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 6-methoxy-1-tetralone (6.0 g, 0.034 moles) in 48% aqueous hydrobromic acid (80 cm3) was refluxed for 2.5 h. The clear orange solution was then cooled to ice temp. and the resulting preicpitate was filtered off under suction, washed with cold water, and dried to afford the title compound as a pale orange solid (5.16 g, 93%), δH [250 MHz: (CD3)2SO] 1.99 (2H, m), 2.47 (2H, t), 2.82 (2H, t), 6.64 (1H, d), 6.71 (1H, dd), 7.73 (1H, d) and 10.31 (1H, broad s, OH).

Workup

  1. temperatureThe clear orange solution was then cooled to ice temp
  2. filtrationand the resulting preicpitate was filtered off under suction
  3. washwashed with cold water
  4. customdried

Sources & evidence

ORD record
ord-fd51ed4e6f8c4f0191cc749dadd920c8
Source dataset
uspto-grants-1998_12
Patent number
US05843989

Reaction notes

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