4-Toluenesulfonyl chloride → HCID 18368347, compound

HRID 379708Notes

Reaction equation

HRID 379708 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7][OH:8].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:8][CH2:7][CH2:6][O:5][C:4]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:3]=2[O:2][CH3:1])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18368290HCID 18368290, compound

Product 1

HCID 18368347HCID 18368347, compoundYield 125.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(2-Methoxy-4-nitrophenoxy)ethanol (12.0 g) and triethylamine (8.9 g) were dissolved into chloroform (60 ml) and p-toluenesulfonyl chloride (12.3 g) was added into this solution. The solution was stirred for 9 hours at room temperature and allowed to stand for one night. The reaction mixture was washed with water (100 ml) two times and dehydrated with anhydrous sodium sulfate and then concentrated under vacuum to dryness to obtain 2-(2-methoxy-4-nitrophenoxy)ethyl p-toluenesulfonate (25.9 g) as yellowish solid.

Workup

  1. additionwas added into this solution
  2. waitto stand for one night
  3. washThe reaction mixture was washed with water (100 ml) two times
  4. concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record
ord-191123560ce5473398246a0f38b14dde
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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