4-Toluenesulfonyl chloride → HCID 20087063, compound

HRID 1608693Notes

Reaction equation

HRID 1608693 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].[C:12]([CH2:14][CH:15]([CH2:18][OH:19])[CH2:16][OH:17])#[N:13].[OH-:20].[Na+]>C1C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[C:12]([CH2:14][CH:15]([CH2:18][O:19][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:2])=[O:20])[CH2:16][O:17][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])#[N:13]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 20087060HCID 20087060, compound

Product 1

HCID 20087063HCID 20087063, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 241BenzeneSolvent

Procedure

A solution of 60 g tosylchloride in 400 ml benzene is added to a stirred and cooled mixture of 17.5 g 2-cyanomethyl1,3 propanediol, 1.3 g triethylbenzylammonium chloride and 150 ml 30% (w/w) aqueous NaOH solution. This mixture is stirred overnight. The organic and aqueous layers are separated and the aqueous layer is washed with diethylether. The combined organic phase is washed with water until neutral, dried and evaporated. 2-Cyanomethyl-1,3-bis(tosyloxy)propane is obtained in a obtained in a yield of 62 g; liquid. Identification by means of IR, NMR and mass spectra.

Workup

  1. temperaturecooled
  2. stirringThis mixture is stirred overnight
  3. customThe organic and aqueous layers are separated
  4. washthe aqueous layer is washed with diethylether
  5. washThe combined organic phase is washed with water until neutral,
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-3cf151e213a042c6bc8fa6bdedd605b0
Source dataset
uspto-grants-1995_03
Patent number
US05395946

Reaction notes

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