4-Methylbenzaldehyde → Pyridinium, 1-methyl-, tetraphenylborate(1-) (1:1)

HRID 2185577Notes

Reaction equation

HRID 2185577 reaction equation
CC1C=CC(C=O)=CC=1.[C:10]1([B-:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[C:36]1[CH:41]=[CH:40][N+:39]([CH3:42])=[CH:38][CH:37]=1>N1CCCCC1.C(O)C>[C:29]1([B-:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1.[CH3:42][N+:39]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 77254-MethylbenzaldehydeHCID 13865068HCID 13865068, compound

Product 1

HCID 11090946Pyridinium, 1-methyl-, tetraphenylborate(1-) (1:1)Yield 78%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

In a 500-mL one-neck flask fitted with a stirrer and a condenser, 1.2 g (0.01 mol) of 4-methylbenzaldehyde, 0.01 mol of 4-methyl-N-methylpyridinium tetraphenylborate, and 30 mL of absolute ethanol were mixed. Five drops of piperidine was added to the mixture. The solution was then heated to reflux, refluxed overnight, cooled, and filtered. The collected solid was washed twice with ether and twice with water to obtain 4-[p-N-methyl-N-ethylamino)styryl]-N-methylpyridinium tetraphenylborate in 78% yield as a reddish solid.

Workup

  1. customIn a 500-mL one-neck flask fitted with a stirrer and a condenser
  2. temperatureThe solution was then heated
  3. temperatureto reflux
  4. temperaturerefluxed overnight
  5. temperaturecooled
  6. filtrationfiltered
  7. washThe collected solid was washed twice with ether and twice with water

Sources & evidence

ORD record
ord-da59c83da15d4c6592f2c999b7403f72
Source dataset
uspto-grants-2002_06
Patent number
US06402037B1

Reaction notes

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