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

HRID 1291841Notes

Reaction equation

HRID 1291841 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 85%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 6-methoxy-1-tetralone (5.0 g) in 48% hydrobromic acid (62 ml) was refluxed for 8 hours. The mixture was cooled, filtered and washed with water (50 ml) to give 6-hydroxy-1-tetralone (3.91 g): NMR δ (d6DMSO) 1.9-2.05(m,2H), 2.4-2.55(m,2H), 2.8-2.9(m,2H), 6.65(d,1H), 6.7(dd,1H), 7.75(d,1H),; m/e 163(M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washwashed with water (50 ml)

Sources & evidence

ORD record
ord-66491d8f3aa54544851fba542ca82aa1
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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