2-Methylnaphthalene → 2-Methyl-1-naphthaldehyde

HRID 434867Notes

Reaction equation

HRID 434867 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[CH3:12][O:13]C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=[O:13]

Participants

5

Reactant 2

HCID 70552-MethylnaphthaleneHCID 21004Methane, dichloromethoxy-

Product 1

HCID 40638272-Methyl-1-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

By the method of Preparation 1, except that a reaction time of 1 hour at 0° C. was employed, 2-methylnaphthalene (10 g., 0.070 mole) in 200 ml. of methylene chloride was reacted with titanium tetrachloride (52.6 g., 30.5 ml., 0.28 mole) and 1,1-dichloromethyl methyl ether (24.1 g., 0.21 mole). The crude product, obtained as an oil, was distilled, yielding 12.2 g. of distillate b.p. 155°-160° C./2.3-3.0 mm. On standing, crystalline product separated from the distillate. Filtration gave purified 2-methyl-1-naphthaldehyde (0.53 g., m.p. 48°-50° C.).

Workup

  1. customBy the method of Preparation 1
  2. customexcept that a reaction time of 1 hour
  3. customat 0° C.

Sources & evidence

ORD record
ord-7805c87598fb4e228a68f05d26aed170
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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