Methane → HCID 22990423, compound

HRID 1384442Notes

Reaction equation

HRID 1384442 reaction equation
C.[C:2]([C:6]1[CH:7]=[C:8](O)[C:9](=[CH:11][CH:12]=1)O)([CH3:5])(C)C.[C:14]1(C)C=CC(S(O)(=O)=O)=C[CH:15]=1.C[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=1[CH3:32]>O>[CH:2]([C:6]1[CH:12]=[CH:11][C:9]([CH2:32][C:31]2[CH:26]=[CH:27][C:28]([CH:14]=[CH2:15])=[CH:29][CH:30]=2)=[CH:8][CH:7]=1)=[CH2:5]

Participants

6

Reactant 4

HCID 297MethaneHCID 6101p-Toluenesulfonic acidHCID 7237O-XyleneHCID 73814-tert-Butylcatechol

Product 1

HCID 22990423HCID 22990423, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 10.02 g (0.0391 mole) of bis-[4-(]-hydroxyethyl)phenyl]-methane (BHEPM) 0.010 g of 4-tert-butyl catechol, 0.125 g (1.248% of BHEPM weight or 5.050 mmole/L) p-toluenesulfonic acid (monohydrate) (TSA), and 120 mL of o-xylene was heated at the boiling temperature for 1.5 hours. Water released during the dehydration was azeotroped from the system. Then, the reaction mixture was washed successively by the distilled water, 2-3% solution of sodium bicarbonate (NaHCO3), and by water again for attaining pH=7. The solution of the product in o-xylene was dried over CaCl2 passed through a layer of alumina, and the solvent removed by distillation under the reduced (1-2 mm Hg) pressure at 40° C. in the presence of about 0.00168 g tert-butyl catechol. The yield of the unsaturated composition riched with bis-(4-vinylphenyl) methane (BVPM) was 7.59 g (88% of theor.), mp 30-33° C., nD40 1.603. According to the reversed phase chromatography (column Separon Si C18, toluene was used as eluate, the elution rate was 0.1 mL minute, a refractometric detector was used). The content of components was as follows, wt-%: Monomer M1 (BVPM) 79, its unsaturated dimer 16.5, its insaturated trimer 4, unsaturated tetramer and higher oligomers <0.5%. The pure BVPM (purity was >99.5%), mp 36-38° C. was obtained by sublimation of the monomer at 130° C. for 1 hour under vacuum (1-2 mmHg).

Workup

  1. temperaturewas heated at the boiling temperature for 1.5 hours
  2. customwas azeotroped from the system
  3. washThen, the reaction mixture was washed successively by the distilled water, 2-3% solution of sodium bicarbonate (NaHCO3)
  4. dry with materialThe solution of the product in o-xylene was dried over CaCl2
  5. customthe solvent removed by distillation under the
  6. customat 40° C.

Sources & evidence

ORD record
ord-64ec0d53be5643219fc5dcf9a0a3eb15
Source dataset
uspto-grants-2001_07
Patent number
US06258909B1

Reaction notes

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