Water → 1,4-Dimethoxy-2-naphthaldehyde

HRID 1790287Notes

Reaction equation

HRID 1790287 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][CH:4]=1.[CH3:15][O:16]C(Cl)Cl.O>ClCCl>[CH3:14][O:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 823371,4-Dimethoxynaphthalene

Product 1

HCID 105848151,4-Dimethoxy-2-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-dimethoxy-naphthalene (5 g, 26.6 mmol) in dichloromethane (100 mL) at 0° C. was added dichloromethyl methyl ether (3.66 g, 31.9 mmol) and stannic chloride (13.8 g, 53.1 mmol). The reaction mixture was stirred for 30 min at this temperature, allowed to warm to room temperature and stirred for an additional 30 min. Water (100 mL) was added and the mixture was extracted with dichloromethane (2×100 mL) and the combined extracts dried (MgSO4). The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, ethyl acetate/hexane: 2/8) to give a white solid: 1H NMR (DMSO-d6) δ 4.06 (s, 3H, CH3), 4.13 (s, 3H, CH3), 7.14 (s, 1H, Ar—H), 7.82 (m, 2H, Ar—H), 8.29 (m, 2H, Ar—H), 10.54 (s, 1H, CHO).

Workup

  1. stirringstirred for an additional 30 min
  2. extractionthe mixture was extracted with dichloromethane (2×100 mL)
  3. dry with materialthe combined extracts dried (MgSO4)
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel, ethyl acetate/hexane: 2/8)
  6. customto give a white solid

Sources & evidence

ORD record
ord-c5390d5a8a25467485038a2668f38edf
Source dataset
uspto-grants-2006_07
Patent number
US07071225B2

Reaction notes

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