1-Chloromethylnaphthalene → HCID 14074782, compound

HRID 620893Notes

Reaction equation

HRID 620893 reaction equation
[CH:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH:1]([N:4]([CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])=[CH:10][CH:11]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 68451-ChloromethylnaphthaleneHCID 10340Sodium CarbonateHCID 21245354HCID 21245354, compound

Product 1

HCID 14074782HCID 14074782, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 g (0.01 mole) of N-(isopropyl)-4-t-butylbenzylamine was dissolved in 50 ml of dry dimethylformamide, and 1.6 g (0.015 mole) of anhydrous sodium carbonate was added. While the mixture was stirred at room temperature, 1.94 g (0.011 mole) of 1-(chloromethyl)-naphthalene was added. The mixture was reacted at 30° to 40° C. for 6 hours. Ice water was added to the reaction mixture, and the mixture was extracted with toluene. The organic layer was washed with water and then toluene was evaporated. The residue was chromatographed on a silica gel column and eluted with 5% ethyl acetate/n-hexane. The eluate was concentrated to give 3.17 g (yield 92%) of an oily substance.

Workup

  1. customThe mixture was reacted at 30° to 40° C. for 6 hours
  2. extractionthe mixture was extracted with toluene
  3. washThe organic layer was washed with water
  4. customtoluene was evaporated
  5. customThe residue was chromatographed on a silica gel column
  6. washeluted with 5% ethyl acetate/n-hexane
  7. concentrationThe eluate was concentrated
  8. customto give 3.17 g (yield 92%) of an oily substance

Sources & evidence

ORD record
ord-2c4784b3ae34450dba3fa06992092ddc
Source dataset
uspto-grants-1989_04
Patent number
US04822822

Reaction notes

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