2-Nitrophenol → 1-(Benzhydryloxy)-2-nitrobenzene

HRID 1270427Notes

Reaction equation

HRID 1270427 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Br-].[C:18]1([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH:24]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 18470978Diphenylmethane bromide

Product 1

HCID 74341221-(Benzhydryloxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of dry ortho-nitrophenol (79 mmol) in 200 ml of acetone there are added 127 mmol of potassium carbonate and also 79 mmol of diphenylmethane bromide. The reaction mixture is heated at reflux for 6 hours and, after the temperature has been lowered to ambient temperature, is stirred further overnight. The reaction mixture is filtered and rinsed with acetone. The filtrate is evaporated and then taken up in diethyl ether and hydrolysed. The aqueous phase is extracted with diethyl ether; the organic phase is then dried over magnesium sulphate, filtered and concentrated. The residue obtained is taken up in petroleum ether, filtered, rinsed with petroleum ether and then dried in vacuo, allowing the expected product to be isolated.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 6 hours
  3. customhas been lowered to ambient temperature
  4. filtrationThe reaction mixture is filtered
  5. washrinsed with acetone
  6. customThe filtrate is evaporated
  7. extractionThe aqueous phase is extracted with diethyl ether
  8. dry with materialthe organic phase is then dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue obtained
  12. filtrationfiltered
  13. washrinsed with petroleum ether
  14. customdried in vacuo
  15. customto be isolated

Sources & evidence

ORD record
ord-e75a3f883be6447f83a4136f484bf8a6
Source dataset
uspto-grants-2007_04
Patent number
US07202255B2

Reaction notes

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