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

HRID 1194951Notes

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 l 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 140°-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 resulting 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 140°-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 resulting crystals were filtered
washwashed with water
washwashed with methanol
customdried

Sources & evidence

ORD record: ord-fb3dbbdba7234d30a11614495d4f467e
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04816516

Reaction notes

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