Benzyl Alcohol → HCID 10903965, compound

HRID 2226635Notes

Reaction equation

HRID 2226635 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:18]([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)([O-:25])(=[O:3])=[O:2].[CH2:18]([N+:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 10903965HCID 10903965, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
5 °C

Procedure

19.07 g (0.1 mol) of tosyl chloride and 15.82 g (0.2 mol) of pyridine were dissolved in 60 g of acetone, and, after cooling to 5° C., there was added 10.81 g (0.1 mol) of benzyl alcohol. While suppressing excessive elevation of the temperature, reaction was allowed for 5 hours. After the completion of the reaction, the mixture was concentrated and the precipitated white solid was washed with ether and dried to give N-benzylpyridinium tosylate. Yield: 80%.

Workup

  1. customelevation of the temperature, reaction
  2. customAfter the completion of the reaction
  3. concentrationthe mixture was concentrated
  4. washthe precipitated white solid was washed with ether
  5. customdried

Sources & evidence

ORD record
ord-f046dce07e9f4d11925e7c60b21bc0c4
Source dataset
uspto-grants-1994_09
Patent number
US05349067

Reaction notes

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