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

HRID 644795Notes

Reaction equation

HRID 644795 reaction equation
[CH2:1]([Cl:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1>C(#N)C>[Cl-:8].[CH2:1]([N+:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 79634-Methylpyridine

Product 1

HCID 10856996Pyridinium, 4-methyl-1-(phenylmethyl)-, chloride (1:1)Yield 93.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.53 g of benzyl chloride (20 mmol), 1.86 g of 4-picoline (20 mmol) and 20 mL of acetonitrile was refluxed for three hours, cooled to room temperature and then frozen in refrigerator. Pale pink crystals precipitated from the solution, which were collected by filtration and washed with ether (3×5 mL) to afford 4.09 g of the product (92% yield). 1HNMR (DMSO-d6, 400 MHz): δ 9.1 (s, 2H), 8.0 (d, 2H, J=6.24), 7.5 (s, 2H), 7.4 (m, 3H), 5.8 (s, 2H), 2.6 (s, 3h); 13C NMR (DMSO-d6, 100 MHz): δ 159.0, 143.5, 134.3, 128.9, 128.8, 128.3, 61.9, 21.1.

Workup

  1. temperaturefrozen in refrigerator
  2. customPale pink crystals precipitated from the solution, which
  3. filtrationwere collected by filtration
  4. washwashed with ether (3×5 mL)

Sources & evidence

ORD record
ord-78c47eaa122c4b3081e0540726fb47d9
Source dataset
uspto-grants-2010_04
Patent number
US07700780B2

Reaction notes

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