4,4'-Dihydroxybiphenyl → Xanthene biphenylene

HRID 2109352

Reaction equation

HRID 2109352 reaction equation
C(O[C:6]1[C:19](C)=[C:18](C)[C:17]2[O:16][C:15]3[C:10](=[C:11](C)[C:12](OCC4OC4)=[C:13](C)[C:14]=3C)[CH:9](C3C=CC=CC=3)[C:8]=2[C:7]=1C)C1OC1.O[C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47](O)=[CH:46][CH:45]=2)=[CH:40][CH:39]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C(=O)C.O>[CH:11]1[C:10]2[CH2:9][C:8]3[C:17](=[CH:18][CH:19]=[CH:6][CH:7]=3)[O:16][C:15]=2[CH:14]=[CH:13][CH:12]=1.[CH:39]1[C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:41]=2[CH:42]=[CH:43][CH:38]=1

Participants

6

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 11776TriphenylphosphineHCID 587469822,7-Diglycidyloxy-1,3,4,5,6,8-hexamethyl-9-phenylxanthene

Product 1

HCID 69049558Xanthene biphenyleneYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

0.972 g (manufactured by DAINIPPON INK & CHEMICALS Co., Ltd., “EXA7335”, 2 mmol) of 2,7-diglycidyloxy-1,3,4,5,6,8-hexamethyl-9-phenylxanthene, 0.372 g (2 mmol) of 4,4′-dihydroxybiphenyl, 2.62 mg (0.01 mmol) of triphenylphosphine and 1.34 g of N,N-dimethylacetamide were reacted under a nitrogen atmosphere at 160° C. for 4 hours. After cooling, the reaction solution was diluted with N,N-dimethylacetamide so as to adjust the nonvolatile content to 15% and then added dropwise in 100 ml of water. The resulting white turbid dispersion was stirred at room temperature for one hour. After the dispersion was centrifuged and suction-filtered, the resulting precipitate was washed with methanol and then vacuum-dried at 60° C. to obtain a xanthene-biphenylene copolymer type linear epoxy resin. The amount of the resulting xanthene-biphenylene copolymer type linear epoxy resin was 1.033 g and the yield was 77%.

Workup

  1. temperatureAfter cooling
  2. filtrationsuction-filtered
  3. washthe resulting precipitate was washed with methanol
  4. customvacuum-dried at 60° C.

Sources & evidence

ORD record
ord-09248beb50824e9fa83a897edd031c34
Source dataset
uspto-grants-2009_04
Patent number
US07514507B2

Linked notes

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