4-Toluenesulfonyl chloride → HCID 2235953, compound

HRID 597123Notes

Reaction equation

HRID 597123 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([OH:12])=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:3]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[OH-].[Na+]>CC(C)=O>[C:13]([C:4]1[CH:3]=[C:2]([NH:1][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH:7]=[C:6]([C:8]([CH3:9])([CH3:10])[CH3:11])[C:5]=1[OH:12])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 2235953HCID 2235953, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 11.05 grams (0.05 mole) of 4-amino-2,6-di-tert-butylphenol in 50 ml of acetone was added with mixing 9.5 grams (0.05 mole) of p-toluenesulfonyl chloride. After the slight exotherm subsided, 10 ml of 5N sodium hydroxide solution was added. During this addition, an oil separated which eventually solidified. An additional 50 ml of water was added, and the product was separated by filtration. The crude product weighed 12.88 grams and melted at 160°-180° C. After recrystallization from methanol/water and ethanol/water, the melting point was 180°-182° C. (Compound 1)

Workup

  1. additionDuring this addition
  2. customan oil separated which
  3. additionAn additional 50 ml of water was added
  4. customthe product was separated by filtration
  5. customAfter recrystallization from methanol/water and ethanol/water

Sources & evidence

ORD record
ord-27ee31d7896c40c2aa78295077658e7d
Source dataset
uspto-grants-1977_03
Patent number
US04013621

Reaction notes

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