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

HRID 1198560Notes

Reaction equation

HRID 1198560 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+].[CH:17](Br)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH:17]([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:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 236603Bromodiphenylmethane

Product 1

HCID 74341221-(Benzhydryloxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Nitrophenol (11.0 g, 79 mmole), anhydrous potassium carbonate (17.6 g, 127.4 mmole) and benzhydryl bromide (19.6 g, 79 mmol) in acetone (220 ml) were refluxed under nitrogen for 5 hours. The mixture was cooled, filtered and evaporated in vacuo. The residue was triturated with diethyl ether, filtered and evaporated. Trituration with 60°-80° C. petroleum ether yielded a brown solid.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe residue was triturated with diethyl ether
  5. filtrationfiltered
  6. customevaporated
  7. customTrituration with 60°-80° C. petroleum ether yielded a brown solid

Sources & evidence

ORD record
ord-bf579edc0ce849fe8869e66392514941
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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