p-Toluenesulfonic acid → HCID 18388460, compound

HRID 1937060Notes

Reaction equation

HRID 1937060 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:23]1([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:23]1([C:29]([C:9]2[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=[CH:7][C:8]=2[OH:11])([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH3:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 73934-tert-ButylphenolHCID 107401,1-Diphenylethylene

Product 1

HCID 18388460HCID 18388460, compound

Conditions

Temperature
110 °C

Procedure

To a 500 mL three-necked flask equipped with a mechanical stirrer, 40 g of 4-tert-butylphenol, 40 g of hexanes and 1.9 g of p-toluenesulfonic acid are charged. The slurry is heated to 60° C. at which time 62 g of 1,1-diphenylethylene is added. The temperature is increased to 110° C. and the hexanes are removed by distillation. After 4.5 hours, the reaction mass is cooled to ambient temperature and purified by silica gel chromatography using heptane/ethyl acetate as the eluent. Sixty (60) grams of the title compound is obtained whose structure is confirmed by 1H nmr.

Workup

  1. customTo a 500 mL three-necked flask equipped with a mechanical stirrer
  2. additionis added
  3. customthe hexanes are removed by distillation
  4. temperaturethe reaction mass is cooled to ambient temperature
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-1b94431dd4a94aa8b5f8606a9f708aad
Source dataset
uspto-grants-2002_05
Patent number
US06392056B1

Reaction notes

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