2-Nitrophenol → Benzyl 2-nitrophenyl ether

HRID 54521

Reaction equation

HRID 54521 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 736266Benzyl 2-nitrophenyl ether

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 2-nitrophenol (13.9 g, 0.10 mol), benzyl bromide (12.0 ml, 0.10 mol) and anhydrous potassium carbonate (30 g, 0.22 mol) in acetone (200 ml) is heated under reflux for 16 hours, cooled, poured onto ice-dilute hydrochloric acid, and extracted with dichloromethane. The extract is dried and evaporated and the residue is crystallized from ether-hexane as pale crystals, m.p. <50° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 16 hours
  3. temperaturecooled
  4. additionpoured onto ice-dilute hydrochloric acid
  5. extractionextracted with dichloromethane
  6. customThe extract is dried
  7. customevaporated
  8. customthe residue is crystallized from ether-hexane as pale crystals, m.p. <50° C.

Sources & evidence

ORD record
ord-e44dbfde469446e78ff3839f598915a5
Source dataset
uspto-grants-1997_04
Patent number
US05622969

Linked notes

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