Nitrobenzene → HCID 57913439, compound

HRID 1261739Notes

Reaction equation

HRID 1261739 reaction equation
O[C:2](C1C=CC=CC=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:3]1[CH:8]=[C:7]([OH:9])[C:6]([C:10](O)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:4]=1[OH:24].[N+]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([O-])=O>>[C:40]1([C:2]2[C:25]3[C:26]([O:24][C:4]4[C:3]=2[CH:8]=[C:7]2[C:6](=[C:10]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=5[O:9]2)[CH:5]=4)=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

3

Reactant 2

HCID 7416NitrobenzeneHCID 57913431HCID 57913431, compound

Product 1

HCID 57913439HCID 57913439, compoundYield 51.2%

Procedure

A flask is charged with 2,5-bis-(hydroxy-diphenyl-methyl)-benzene-1,4-diol (Example 1) (9.5 g) and nitrobenzene (50 g). The obtained suspension is heated at reflux for ca. 45 minutes, and then allowed to cool over night. The formed crystals are filtered off, washed several times with ethanol and dried at 10−3 mbar/190° C. for two hours (some sublimation takes place) to give 4.47 g of greenish red crystals, mp.=419° C. (DSC). Elementary analysis: Ccalcd. 88.05%, Cfound 87.62% and 87.78%; Hcalcd. 4.62%, Hfound 4.29% and 4.65%. The proposed structure is confirmed by an X-ray crystal structure, monoclinic, space group C2/c, a=18.961(5), b=6.058(2), c=20.229 (5); alpha=90.00, beta=116.351(9), gamma=90.00; Z=4.

Workup

  1. temperatureThe obtained suspension is heated
  2. temperatureat reflux for ca. 45 minutes
  3. temperatureto cool over night
  4. filtrationThe formed crystals are filtered off
  5. washwashed several times with ethanol
  6. customdried at 10−3 mbar/190° C. for two hours (some sublimation

Sources & evidence

ORD record
ord-710bd31fbb4d4f01ba0ab59681017e38
Source dataset
uspto-grants-2013_06
Patent number
US08471019B2

Reaction notes

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