Water → HCID 4767210, compound

HRID 650978Notes

Reaction equation

HRID 650978 reaction equation
[Na].[O:2]=[CH:3][C:4]1[CH:12]=[CH:11][C:9](O)=[C:6]([O:7][CH3:8])[CH:5]=1.Cl[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.[OH2:25]>CO>[CH3:8][O:7][C:6]1[C:5]([O:25][CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[C:4]([CH:12]=[CH:11][CH:9]=1)[CH:3]=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 68451-ChloromethylnaphthaleneHCID 5360545Sodium

Product 1

HCID 4767210HCID 4767210, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5 g of sodium are dissolved in 200 ml of methanol. 30.4 g of vanillin are metered into the resulting solution. The reaction mixture is stirred at room temperature for 30 minutes. 36 g of 1-chloromethylnaphthalene in 70 ml of methanol are then added and the reaction mixture is heated at reflux for 6 hours. The mixture is left to stand overnight and then introduced into 1 liter of water. Extraction is carried out twice using 700 ml of ethyl acetate each time. The organic phases are washed twice using 200 ml of ice-cold 2N sodium hydroxide solution each time and once with 200 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated, yielding 3-methoxy(naphthalen-1-ylmethoxy)-benzaldehyde, which can be purified by chromatography on silica gel with ethyl acetate/n-hexane 1:2 and recrystallisation from ethyl acetate/n-hexane, m.p. 98-99° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 6 hours
  3. waitThe mixture is left
  4. waitto stand overnight
  5. extractionExtraction
  6. washThe organic phases are washed twice
  7. dry with materialonce with 200 ml of saturated sodium chloride solution, dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ec9b5da5e9254c34875598644d208203
Source dataset
uspto-grants-2001_08
Patent number
US06277849B1

Reaction notes

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