p-Toluenesulfonic acid → HCID 22507796, compound

HRID 1861573Notes

Reaction equation

HRID 1861573 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[CH:10]([OH:14])[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.N(C1CCN(C)C(C)(C)C1C)C(C)=O>ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[C:10](=[O:14])[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 68508215,7-Di-tert-butyl-3-hydroxy-2-benzofuranoneHCID 18620266HCID 18620266, compound

Product 1

HCID 22507796HCID 22507796, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.8 g (0.0146 mol) of 5,7-di-tert-butyl-3-hydroxy-benzofuranone, 6.1 g (0.032 mol) of p-toluenesulfonic acid and 6.9 g (0.032 mol) of 4-acetamino-tetramethylpiperidine (TEMPO) are stirred in 100 ml of dichloromethane at room temperature for 24 hours. The yellow solution is then washed three times with 200 ml of 5% hydrochloric acid each time, dried over magnesium sulfate and concentrated to dryness by evaporation. Crystallisation of the residue from hexane yields 1 g of the above-mentioned compound.

Workup

  1. washThe yellow solution is then washed three times with 200 ml of 5% hydrochloric acid each time
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness by evaporation
  4. customCrystallisation of the residue from hexane

Sources & evidence

ORD record
ord-2a4801e29a714bc4a8dd603acbd41104
Source dataset
uspto-grants-2003_03
Patent number
US06533825B2

Reaction notes

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