Dimethylformamide → 2-Methoxy-1-naphthaldehyde

HRID 542156Notes

Reaction equation

HRID 542156 reaction equation
[CH3:1]N(C)C=O.[OH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[CH:17]=[O:18].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(OC)(=O)=O)=CC=1>O>[CH3:1][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[CH:17]=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 128192-Hydroxy-1-naphthaldehyde

Product 1

HCID 793522-Methoxy-1-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

500 ml of a dimethylformamide solution containing 103.2 g (0.6 mole) of 2-hydroxy-1-naphthaldehyde and 107.6 g (0.78 mole) of anhydrous potassium carbonate was stirred with heating at 50° C. To the solution was added dropwise 145 g (0.78 mole) of methyl p-toluenesulfonate. After the completion of the dropwise addition, the mixture was stirred at 60° C. for 2 hours. The reaction mixture was added to 1.5 liters of water, and the precipitated crystals were collected by filtration. The crude crystals were recrystallized from a solvent mixture of n-hexane and ethyl acetate (5/1 by volume) to obtain 93.8 g (0.504 mole) of 2-methoxy-1-naphthaldehyde.

Workup

  1. additionAfter the completion of the dropwise addition
  2. stirringthe mixture was stirred at 60° C. for 2 hours
  3. filtrationthe precipitated crystals were collected by filtration
  4. customThe crude crystals were recrystallized from a solvent mixture of n-hexane and ethyl acetate (5/1 by volume)

Sources & evidence

ORD record
ord-5dcee47e4d384ae9bd87e7df56f0487b
Source dataset
uspto-grants-1987_04
Patent number
US04656126

Reaction notes

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