4-Toluenesulfonyl chloride → HCID 54143332, compound

HRID 374813Notes

Reaction equation

HRID 374813 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5]O)[CH3:2].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.C(OCC)(=[O:20])C>N1C=CC=CC=1>[CH2:1]([O:3][CH2:4][CH2:5][C:8]1[CH:9]=[C:10]([S:13]([OH:20])(=[O:15])=[O:14])[CH:11]=[CH:12][C:7]=1[CH3:17])[CH3:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8076Glycol monoethyl etherHCID 8857Ethyl Acetate

Product 1

HCID 54143332HCID 54143332, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2 g of 2-ethoxyethanol were dissolved in 40 ml of pyridine, to which 5.66 g of p-toluenesulfonyl chloride was added under ice-cooling conditions, followed by raising to room temperature. Ethyl acetate was added, followed by washing with water and a saturated sodium hydrogencarbonate aqueous solution and drying with anhydrous magnesium sulfate. This was filtered and, after removal of the solvent by distillation, the resultant residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:hexane=5:95) to obtain 3.69 g of the captioned compound (yield 56%).

Workup

  1. additionwas added under ice-
  2. temperaturecooling conditions
  3. washby washing with water
  4. dry with materiala saturated sodium hydrogencarbonate aqueous solution and drying with anhydrous magnesium sulfate
  5. filtrationThis was filtered
  6. customafter removal of the solvent
  7. distillationby distillation

Sources & evidence

ORD record
ord-08e39c04a2c74fb796240d9353ad0813
Source dataset
uspto-grants-1996_01
Patent number
US05482937

Reaction notes

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