Water → 7-Cyano-2-methoxy-1-naphthaldehyde

HRID 1954214Notes

Reaction equation

HRID 1954214 reaction equation
[C:1]([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)#[N:2].[CH3:15][O:16]C(Cl)Cl.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]2[C:10]([CH:9]=[CH:8][C:7]([O:13][CH3:14])=[C:6]2[CH:15]=[O:16])=[CH:11][CH:12]=1)#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 109541837-Methoxy-2-naphthonitrile

Product 1

HCID 226276417-Cyano-2-methoxy-1-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, 3.7 g of 2-cyano-7-methoxynaphthalene was dissolved in 40 ml of dichloro-methane, and 6.6 ml of titanium tetrachloride and 4.6 ml of dichloromethyl methyl ether were added dropwise into the resulting solution at 0° C. in this order. The resulting mixture was stirred at room temperature for 30 minutes and cooled to 0° C. again. Water was added to the resulting mixture to cease the reaction, and the resulting mixture was extracted with dichloromethane (100 ml×2). The organic layers were combined, washed with water, a saturated aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated and the resulting crude crystal was washed with ether and dried to give 3.3 g of the title compound as colorless crystals.

Workup

  1. temperaturecooled to 0° C. again
  2. customthe reaction
  3. extractionthe resulting mixture was extracted with dichloromethane (100 ml×2)
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. washthe resulting crude crystal was washed with ether
  9. customdried

Sources & evidence

ORD record
ord-c5c216276988407eb213d0789471d93e
Source dataset
uspto-grants-2000_09
Patent number
US06121309

Reaction notes

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