O-Xylene → 4,4'-DIVINYLBIPHENYL

HRID 1857085Notes

Reaction equation

HRID 1857085 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-b9fda63a35624064a4208182473a397e
Source dataset
uspto-grants-2000_11
Patent number
US06143922

Reaction notes

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