Bisphenol A → 2,2-Bis[4-(3-nitrophenoxy)phenyl]propane

HRID 1194953Notes

Reaction equation

O[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[N+]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1)([O-])=O.[C:30](=[O:33])([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:27]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:33][C:30]3[CH:26]=[CH:21][CH:22]=[C:23]([N+:27]([O-:29])=[O:28])[CH:24]=3)=[CH:3][CH:4]=2)([CH3:10])[CH3:9])=[CH:12][CH:13]=1)([O-:29])=[O:28]

Participants

Conditions

Temperature: 65 °C

Procedure

A 1 l glass reaction vessel was charged with 85.6 grams (0.375 mol) of 2,2-bis(4-hydroxyphenyl)propane, 151.2 grams (0.9 mol) of m-dinitrobenzene, 124.6 grams of potassium carbonate and 660 ml of N,N-dimethyl formamide. The mixture was reacted for 10 hours at a temperature for 140°-150° C. 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 450 ml of methanol and stirred for an hour. The resulted crystals were filtered, washed with water, washed with methanol, and dried to obtain 164.8 grams (93.5% yield) of 2,2-bis[4-(3-nitrophenoxy)phenyl]propane as brown crystals.

Workup

customThe mixture was reacted for 10 hours at a temperature for 140°-150° C
customthe reaction
filtrationfiltered
customto remove potassium nitrite
distillationThe solvent was distilled off from the filtrate under reduced pressure
additionadded with 450 ml of methanol
filtrationThe resulted crystals were filtered
washwashed with water
washwashed with methanol
customdried

Sources & evidence

ORD record: ord-ccf4d2811ae44a8b90645ef8861a36b5
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04816516

Reaction notes

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