Benzyl Alcohol → HCID 21910218, compound

HRID 2226636Notes

Reaction equation

HRID 2226636 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].[CH3:12][N:13]([CH3:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.[CH2:28]([OH:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)([O-:35])(=[O:3])=[O:2].[CH2:28]([N+:13]([CH3:20])([CH3:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 949N,N-DimethylanilineHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 21910218HCID 21910218, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

19.07 g (0.1 mol) of tosyl chloride, 12.12 g (0.1 mol) of N,N-dimethylaniline and 10.1 g (0.1 mol) of triethylamine were dissolved in 60 g of tetrahydrofuran, and, after cooling to 10° C., there was added 10.81 g (0.1 mol) of benzyl alcohol. While suppressing excessive elevation of the temperature, the 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-benzyl-N,N-dimethylanilinium tosylate. Yield: 70%.

Workup

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

Sources & evidence

ORD record
ord-807ef9d8256d4330b7ae5466c7f98255
Source dataset
uspto-grants-1994_09
Patent number
US05349067

Reaction notes

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