p-Toluenesulfonic acid → HCID 18620267, compound

HRID 1861575Notes

Reaction equation

HRID 1861575 reaction equation
[CH2:1]1[CH2:6][C:5](=[C:7]2[C:17](=[C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:11]3[CH:12]([OH:16])[C:13](=[O:15])[O:14][C:10]=3[C:9]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8]2)[CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N(C1CCN(C)C(C)(C)C1C)C(C)=O>ClCCl>[CH2:3]1[CH2:4][C:5](=[C:7]2[C:17](=[C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:11]3[C:12](=[O:16])[C:13](=[O:15])[O:14][C:10]=3[C:9]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8]2)[CH2:6][CH2:1][CH2:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 18620266HCID 18620266, compoundHCID 86585513HCID 86585513, compound

Product 1

HCID 18620267HCID 18620267, compoundYield 136.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.1 g (0.01 mol) of bis(5-cyclo-hexylidene)-7-tert-butyl-3-hydroxy-benzofuranone (U.S. Pat. No. 5,614,572, compound 107, Table 1), 8.75 g (0.046 mol) of p-toluenesulfonic acid and 9.8 g (0.046 mol) of 4-acetamino-tetramethylpiperidine (TEMPO) are stirred in 60 ml of dichloromethane at room temperature for 48 hours. The yellow solution is then washed with 50 ml of 5% hydrochloric acid and 4×50 ml of water, dried over magnesium sulfate and concentrated to dryness by evaporation. The residue is dissolved in 100 ml of toluene, and the solution is heated under reflux for 1 hour and then concentrated by evaporation again, yielding 5 g of the abovementioned compound.

Workup

  1. washThe yellow solution is then washed with 50 ml of 5% hydrochloric acid and 4×50 ml of water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness by evaporation
  4. dissolutionThe residue is dissolved in 100 ml of toluene
  5. temperaturethe solution is heated
  6. temperatureunder reflux for 1 hour
  7. concentrationconcentrated by evaporation again

Sources & evidence

ORD record
ord-f38fa70f5a7c471f9ce9895efcb1dd30
Source dataset
uspto-grants-2003_03
Patent number
US06533825B2

Reaction notes

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