4-Toluenesulfonyl chloride → HCID 18368336, compound

HRID 379716Notes

Reaction equation

HRID 379716 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([CH3:15])[C:3]=1[O:4][CH2:5][CH2:6][OH:7].C(N(CC)CC)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([O:7][CH2:6][CH2:5][O:4][C:3]2[C:2]([CH3:1])=[CH:11][C:10]([N+:12]([O-:14])=[O:13])=[CH:9][C:8]=2[CH3:15])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18368274HCID 18368274, compound

Product 1

HCID 18368336HCID 18368336, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-(2,6-Dimethyl-4-nitrophenoxy)ethanol (22 g) was dissolved into chloroform (200 ml) and triethylamine (20 ml) was added into this solution. Further, p-toluenesulfonylchloride (24.5 g) solution in chloroform (100 ml) was added into this solution in an ice bath. After being stirred for 6 hours at room temperature, the reaction mixture was washed with water (150 ml), 1N HCl (150 ml) and then 1N sodium hydroxide (150 ml). After being dehydrated with anhydrous magnesium sulfate (20 g), the solution was concentrated under vacuum to remove chloroform and residue was dissolved into ethyl acetate (50 ml). Hexane (200 ml) was added into ethyl acetate solution and separated solids were collected by filtration. Solids were dried under vacuum to obtain 2-(2,6-dimethyl-4-nitrophenoxy)ethyl p-toluenesulfonate (21.6 g) as yellowish solid.

Workup

  1. additionwas added into this solution
  2. washthe reaction mixture was washed with water (150 ml), 1N HCl (150 ml)
  3. concentrationthe solution was concentrated under vacuum
  4. customto remove chloroform and residue
  5. dissolutionwas dissolved into ethyl acetate (50 ml)
  6. additionHexane (200 ml) was added into ethyl acetate solution
  7. customseparated solids
  8. filtrationwere collected by filtration
  9. customSolids were dried under vacuum

Sources & evidence

ORD record
ord-49240bb1612c4530a1d2333d75c7a442
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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