Benzyl Chloride → Pyridinium, 4-methyl-1-(phenylmethyl)-, chloride (1:1)

HRID 2122038Notes

Reaction equation

HRID 2122038 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([Cl:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CC(C)=O>[Cl-:15].[CH2:8]([N+:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 79634-Methylpyridine

Product 1

HCID 10856996Pyridinium, 4-methyl-1-(phenylmethyl)-, chloride (1:1)Yield 64.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4-methylpyridine (26 mL/0.268 mol) in 70 mL of acetone was added 31 mL (0.268 mol) of benzylchloride. The resulting mixture was stirred at 50° C. for 18 hours. After cooling to room temperature, the reaction was filtered, washed with acetone and dried under reduced pressure affording 38 g of the title compound. The filtrate was concentrated under reduced pressure producing an additional 5.6 grams of the title compound (74% combined yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction was filtered
  3. washwashed with acetone
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ba7de6027050439db4f27ba070d5c6b5
Source dataset
uspto-grants-2004_02
Patent number
US06696567B2

Reaction notes

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