4,4'-Dihydroxybiphenyl → 4,4'-Bis(3-nitrophenoxy)biphenyl

HRID 231616

Reaction equation

O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N+]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1)([O-])=O.[C:27](=[O:30])([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:30][C:27]3[CH:23]=[CH:18][CH:19]=[C:20]([N+:24]([O-:26])=[O:25])[CH:21]=3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)([O-:26])=[O:25]

Participants

Conditions

Temperature: 65 °C

Procedure

A 3 liter glass reaction vessel was charged with 186 grams (1.0 mol) of 4,4'-dihydroxybiphenyl, 438 grams (2.6 mols) of m-dinitrobenzene, 363 grams of potassium carbonate and 2,000 ml of N,N-dimethylformamide. The mixture was reacted at a temperature of 145°-150° C. for 16 hours. After completing the reaction, the resultant mixture was cooled and filtered to remove potassium nitrite. The solvent was distilled off from the filtrate under reduced pressure. The residue was cooled to 65° C., added with 2,000 ml of methanol and stirred for an hour. The resulted crystals were filtered, washed with water, washed with methanol and dried to obtain 426 grams (99.5% yield) of 4,4'-bis(3-nitrophenoxy)biphenyl as brown crystals.

Workup

customThe mixture was reacted at a temperature of 145°-150° C. for 16 hours
customthe reaction
filtrationfiltered
customto remove potassium nitrite
distillationThe solvent was distilled off from the filtrate under reduced pressure
additionadded with 2,000 ml of methanol
filtrationThe resulted crystals were filtered
washwashed with water
washwashed with methanol
customdried

Sources & evidence

ORD record: ord-ce659955b949483983e33552a15ad669
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04847311

Linked notes

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