2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13370663, compound

HRID 2412971Notes

Reaction equation

HRID 2412971 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:13][C:12]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:11][CH2:10]2)=[CH:5][CH:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:12]2[CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:10][CH:11]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13370662HCID 13370662, compound

Product 1

HCID 13370663HCID 13370663, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 13.91 g. of 1-[4,5-bis(4-methoxyphenyl)-1,5-cyclohexadien-1-yl]-4-fluorobenzene in 500 ml. of toluene were added 9.08 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The solution was allowed to reflux under a nitrogen atmosphere for 20 hours employing a Dean-Stark trap. After cooling, the reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by chromatography. The appropriate fractions were combined, evaporated, and recrystallized from diethyl ether/Skelly B to provide 6.08 g. of the desired product as a yellow solid, m.p. about 107°-110° C.

Workup

  1. temperatureto reflux under a nitrogen atmosphere for 20 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by chromatography
  6. customevaporated
  7. customrecrystallized from diethyl ether/Skelly B
  8. customto provide 6.08 g

Sources & evidence

ORD record
ord-9d696a05b6f844e2a7703bbb423b392b
Source dataset
uspto-grants-1985_01
Patent number
US04495202

Reaction notes

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