(1,4-Dimethoxynaphthalen-3-yl)methanol → 1,4-Dimethoxy-2-naphthaldehyde

HRID 1990799Notes

Reaction equation

HRID 1990799 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH2:15][OH:16]>ClCCl.O=[Mn]=O>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH:15]=[O:16]

Participants

4

Reactant 1

HCID 10704023(1,4-Dimethoxynaphthalen-3-yl)methanol

Product 1

HCID 105848151,4-Dimethoxy-2-naphthaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by treating (1,4-dimethoxy-naphthalen-2-yl)-methanol (6.5 g, 29.8 mmol, 1.0 equiv, [CAS RN 150556-57-3], prepared as described in C. Flader, J. Liu, R. F. Borch J. Med. Chem. 2000, 43, 3157-3167) with activated MnO2 (25.9 g, 297.8 mmol, 10.0 equiv) in dichloromethane for 4 h, after which time the reaction was filtered through Hyflo Super Cel and concentrated by evaporation of the solvent under reduced pressure affording 5.1 g (81%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 4.02 (s, 3H), 4.10 (s, 3H), 7.14 (s, 1H), 7.61-7.65 (m, 2H), 8.18-8.30 (m, 2H), 10.58 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. filtrationafter which time the reaction was filtered through Hyflo Super Cel
  3. concentrationconcentrated by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-e7b8d154f42e46d0960b38a1d55293ef
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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