1-Methoxy-2-naphthalenemethanol → 1-Methoxynaphthalene-2-carbaldehyde

HRID 1790295Notes

Reaction equation

HRID 1790295 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[O:13][CH3:14].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:14][O:13][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 45591511-Methoxy-2-naphthalenemethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 131199931-Methoxynaphthalene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product from Step B (4 g, 27.28 mmol) was dissolved in dichloromethane (100 mL) and cooled to 0° C. To this solution was added pyridinium chlorochromate (5.5 g, 25.53 mmol) and the reaction was stirred at this temperature for 1 h. The reaction mixture was washed with 1 M aqueous solution of hydrogen chloride. The organic layer was separated, dried (MgSO4), and concentrated to give an oil, which was purified by flash chromatography (silica gel, ethyl acetate/hexane: 1/9): 1H NMR (CDCl3) δ 4.15 (s, 3H, CH3), 7.61 (m, 3H, Ar—H), 7.87 (m, 2H, Ar—H), 8.28 (m, 1H, Ar—H), 10.61 (s, 1H, CHO); MS 191 (M+NH4+).

Workup

  1. washThe reaction mixture was washed with 1 M aqueous solution of hydrogen chloride
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give an oil, which
  6. customwas purified by flash chromatography (silica gel, ethyl acetate/hexane: 1/9)

Sources & evidence

ORD record
ord-c876af2d9b2c4dcc8051aa884d4c2ab1
Source dataset
uspto-grants-2006_07
Patent number
US07071225B2

Reaction notes

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