O-Xylene → 4,4'-DIVINYLBIPHENYL

HRID 1384443Notes

Reaction equation

HRID 1384443 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 5.0020 g (0.02064 mole) of 4,4′-di-(1-hydroxyethyl)biphenyl (DHEBP), 0.0050 g (0.1% of DHEBP weight) of 4-tert-butyl catechol, 00742 g (1.483% of DHEBP weight or 4.11 mmol/L) of TSA, and 90 mL of o-xylene was heated at the boiling temperature for 40 minutes. 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 3.8 g (89.3% of theor.). According to reversed phase chromatography, the content of components was as follows, wt-%: Monomer M1 (DVBP) 77, its unsaturated dimer 17, its insaturated trimer 5%, tetramers and higher oligomers <1%. 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 40 minutes
  2. customwas azeotroped from the system
  3. additionThen, the reaction mixture was treated

Sources & evidence

ORD record
ord-b07999b14bd944dd9f66f75ef7757183
Source dataset
uspto-grants-2001_07
Patent number
US06258909B1

Reaction notes

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