O-Xylene → 4,4'-DIVINYLBIPHENYL

HRID 1384444Notes

Reaction equation

HRID 1384444 reaction equation
O[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16](O)[CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)[CH3:3].C(C1C=C(O)C(=CC=1)O)(C)(C)C.CC1C=CC=CC=1C>O>[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)=[CH2:3]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 73814-tert-ButylcatecholHCID 618022HCID 618022, compound2×

Product 1

HCID 109874454,4'-DIVINYLBIPHENYL

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 5.00 g (0.0206 mole) of 4,4′-di-(1-hydroxyethyl)biphenyl (DHEBP), 0.0050 g (0.1% of DHEBP weight) of 4-tert-butyl catechol, 00542 g (1.08% of DHEBP weight or 3.00 mmol/L) of TSA, and 90 mL of o-xylene was heated at the boiling temperature for 1 hour. Water released during the dehydration was azeotroped from the system. Then, the reaction mixture was treated as described in Example 1. The yield of the unsaturated composition riched with 4,4′-divinylbiphenyl (DVBP) was 4.10 g (96.5% of theor.). According to reversed phase chromatography, the content of components was as follows, wt-%: Monomer M1 (DVBP) 89, its unsaturated dimer 8.5, its insaturated trimer 2%, tetramers and higher oligomers <0.5%. The pure DVBP (purity was >99.5%), mp 150-153° C. was obtained by sublimation of the monomer at 160° C. for 1 hour under vacuum (1-2 mm Hg).

Workup

  1. temperaturewas heated at the boiling temperature for 1 hour
  2. customwas azeotroped from the system
  3. additionThen, the reaction mixture was treated

Sources & evidence

ORD record
ord-5aab5b7f52cf4b5c8eb3b67df30e92b5
Source dataset
uspto-grants-2001_07
Patent number
US06258909B1

Reaction notes

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