4-Toluenesulfonyl chloride → HCID 2235953, compound

HRID 1707838Notes

Reaction equation

HRID 1707838 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])[NH:8][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 2235953HCID 2235953, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

Dissolve 3,5-di-t-butyl-4-hydroxy-aniline (2.21 g, 10 mmol) in anhydrous pyridine (25 mL) and cool to 5° C. Add, by dropwise addition, p-toluenesulfonyl chloride (2.1 g, 11 mmol) and stir overnight. Partition between water and ethyl acetate and separate the organic phase. Wash the organic phase with cold 1N hydrochloric acid, saturated sodium hydrogen carbonate and brine. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound.

Workup

  1. customPartition between water and ethyl acetate
  2. customseparate the organic phase
  3. washWash the organic phase with cold 1N hydrochloric acid, saturated sodium hydrogen carbonate and brine
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-7ad7fd12cf2c496191992ee9b8defff2
Source dataset
uspto-grants-1994_10
Patent number
US05354782

Reaction notes

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