4-Toluenesulfonyl chloride → HCID 86623646, compound

HRID 2080546Notes

Reaction equation

HRID 2080546 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:11])[C:9]#[N:10].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:11][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9]#[N:10])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 98989362-(2-CHLOROPHENYL)-2-HYDROXYACETONITRILE

Product 1

HCID 86623646HCID 86623646, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2-chlorophenyl)-2-hydroxyacetonitrile (16.8 g, 0.1 mol) and 4-toluene sulfonyl chloride (21 g, 0.11 mol) was dissolved in toluene (100 mL) in a suitable reaction flask. Aqueous 5% NaOH (100 g, 0.125 mol) was added dropwise at 0-5° C. and the reaction continued at 10-15° C. until the reaction was completed by TLC monitoring. The organic layer was separated and the aqueous layer was extracted with toluene (50 ml×2). The combined organic layer was washed with water. After removal of toluene under reduced pressure, the target product was obtained (29 g, yield 90.6%).

Workup

  1. customcontinued at 10-15° C. until the reaction
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with toluene (50 ml×2)
  4. washThe combined organic layer was washed with water
  5. customAfter removal of toluene under reduced pressure
  6. customthe target product was obtained (29 g, yield 90.6%)

Sources & evidence

ORD record
ord-89fecc4c8f084b7184349aec087c4838
Source dataset
uspto-grants-2011_04
Patent number
US07932391B2

Reaction notes

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