Methane, dichloromethoxy- → 2,7-Dimethoxy-1-naphthaldehyde

HRID 727419Notes

Reaction equation

HRID 727419 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:13][CH3:14])=[CH:8][CH:9]=2)[CH:4]=1.[CH3:15][O:16]C(Cl)Cl>ClCCl.Cl[Ti](Cl)(Cl)Cl>[CH3:14][O:13][C:7]1[CH:8]=[CH:9][C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[C:6]=1[CH:15]=[O:16]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 770212,7-Dimethoxynaphthalene

Product 1

HCID 2932152,7-Dimethoxy-1-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

The 2,7-dimethoxynaphthalene 2 (65 mmol; 12.26 g) is dissolved in 150 cm3 of anhydrous dichloromethane under an inert atmosphere. TiCl4 (91 mmol; 10cm3) is added by syringe, at 0° C., followed by dropwise addition, by means of a dropping funnel, of α,α-dichloromethyl methyl ether (99 mmol; 9 cm3) in solution in 40 cm3 of the same solvent. Stirring is continued at 0° C. for 1 h and then at room temperature for 4 h 30. The reaction medium is poured onto an ice/3N HCl mixture (250 cm3), stirred vigorously and then extracted with CH2Cl2. The organic phase is washed with water and then with saturated NaHCO3 solution. The organic phase is dried over MgSO4 and evaporated. The residue is taken up in ether, the solution is filtered and the filtrate is evaporated to dryness. 2,7-Dimethoxynaphthaldehyde 3 is isolated pure in the form of a beige-colored powder.

Workup

  1. waitat room temperature for 4 h 30
  2. stirringstirred vigorously
  3. extractionextracted with CH2Cl2
  4. washThe organic phase is washed with water
  5. dry with materialThe organic phase is dried over MgSO4
  6. customevaporated
  7. filtrationthe solution is filtered
  8. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-d11bd4061662452d84eeab80fa1de7f5
Source dataset
uspto-grants-1998_01
Patent number
US05712312

Reaction notes

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