Dimethylformamide → 2-(benzyloxy)-1-naphthaldehyde

HRID 542158Notes

Reaction equation

HRID 542158 reaction equation
CN(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+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O.C(OCC)(=O)C>[CH2:25]([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])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 128192-Hydroxy-1-naphthaldehyde

Product 1

HCID 7354602-(benzyloxy)-1-naphthaldehydeYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

450 ml of a dimethylformamide solution containing 100 g (0.58 mole) of 2-hydroxy-1-naphthaldehyde and 96.3 g (0.7 mole) of anhydrous potassium carbonate was stirred with heating at 60° C. To the solution was added dropwise 88.3 g (0.7 mole) of benzyl chloride. After the completion of the dropwise addition, the mixture was stirred at 60° C. for 2 hours. Then 870 ml of ethyl acetate heated at 60° C. and 1.2 liters of warm water at 60° C. were added to the mixture and it was extracted at 60° C. and separated. The organic layer was concentrated under reduced pressure to about 550 ml. 440 ml of methanol was added to the concentrate, and the solution was cooled to 5° C. to crystallize. The precipitated crystals were collected by filtration, and washed with methanol to obtain 131 g (0.5 mole) of 2-benzyloxy-1-naphthaldehyde.

Workup

  1. additionAfter the completion of the dropwise addition
  2. stirringthe mixture was stirred at 60° C. for 2 hours
  3. extractionwas extracted at 60° C.
  4. customseparated
  5. concentrationThe organic layer was concentrated under reduced pressure to about 550 ml
  6. addition440 ml of methanol was added to the concentrate
  7. temperaturethe solution was cooled to 5° C.
  8. customto crystallize
  9. filtrationThe precipitated crystals were collected by filtration
  10. washwashed with methanol

Sources & evidence

ORD record
ord-7ca18270cb5a4620acd769e1c8b35dfc
Source dataset
uspto-grants-1987_04
Patent number
US04656126

Reaction notes

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