4-Toluenesulfonyl chloride → 2,6-Dinitro-4-t-butyl-phenyl (4-methyl)-benzenesulfonate

HRID 347447Notes

Reaction equation

HRID 347447 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[C:5]=1[OH:17])([O-:3])=[O:2].[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:17][C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([C:10]([CH3:13])([CH3:11])[CH3:12])=[CH:7][C:6]=2[N+:14]([O-:16])=[O:15])(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 200424-tert-Butyl-2,6-dinitrophenolHCID 81531Diisopropylethylamine

Product 1

HCID 586041142,6-Dinitro-4-t-butyl-phenyl (4-methyl)-benzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-dinitro-4-t-butyl-phenol (80 mmol; 10) and tosyl chloride (80 mmol) were dissolved in 300 ml CH2Cl2. Diisopropylethylamine (DIEA, 80 mmol) was added to the solution. The mixture was stirred at room temperature for 2 hours. The solution was washed with 10% citric acid, saturated aqueous NaCl (sat. NaCl), and dried with MgSO4. The solvent was removed under reduced pressure, and the product was obtained as a bright yellow solid in quantitative yield. 1H NMR (500 MHz, CDCl3): δ=8.12 (s, 2H), 7.80 (d, 2H), 7.40 (d, 2H), 2.51(s, 3H), 1.41 (s, 9H). ESI-MS: m/z: 417.2 (M+Na+).

Workup

  1. washThe solution was washed with 10% citric acid, saturated aqueous NaCl (sat. NaCl)
  2. dry with materialdried with MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customthe product was obtained as a bright yellow solid in quantitative yield

Sources & evidence

ORD record
ord-882622c9ff944599ad42fcda9ad8a234
Source dataset
uspto-grants-2007_02
Patent number
US07173102B2

Reaction notes

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