5-Methoxytetralone → 5-Methoxynaphthalen-1-ol

HRID 2086128Notes

Reaction equation

HRID 2086128 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13]>[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[OH:13]

Participants

3

Reactant 1

HCID 366205-Methoxytetralone

Product 1

HCID 110629015-Methoxynaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a 2000 ml flask a mixtuere of 5-methoxy-1-tetralone (30.0 g, 170.2 mmol) and 10% Pd/C (40 g) in 1000 ml p-cymenewas brought to reflux and monitored by LC-MS until no more starting material was present (approx. 24 h). The mixture was then cooled to room temperature and passed through a silica gel/celite plug and concentrated under vacuum to 26.6 g (90%) of an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ 3.90 (3H, s), 6.83 (1H, appd, J=7.5 Hz), 6.89 (1H, appd, J=7.7 Hz), 7.24 (1H, appt), 7.30 (1H, appt), 7.54 (1H, appd, J=8.5 Hz), 7.65 (1H, d, J=8.5 Hz), 9.98 (1H, s).

Workup

  1. temperatureto reflux
  2. custom(approx. 24 h)
  3. concentrationconcentrated under vacuum to 26.6 g (90%) of an off-white solid

Sources & evidence

ORD record
ord-2abf5cff36a74c2aa3a5f459bda5d91c
Source dataset
uspto-grants-2004_04
Patent number
US06723747B2

Reaction notes

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