2-Nitrophenol → Benzyl 2-nitrophenyl ether

HRID 1196958Notes

Reaction equation

HRID 1196958 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[OH-].[K+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Br-].[K+]>C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 69472-NitrophenolHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 253877Potassium Bromide

Product 1

HCID 736266Benzyl 2-nitrophenyl etherYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A slurry of 41.7 g (0.3 mol) of o-nitrophenol in 200 ml of ethanol was added to a stirred, cooled solution of 19.8 g (0.3 mol) of 85% potassium hydroxide in 300 ml of ethanol; a voluminous yellow-orange precipitate of the potassium salt separated. After stirring at room temperature for 45 minutes, a solution of 35.7 ml (0.3 mol) of benzyl bromide in 100 ml of ethanol was added portionwise (no temperature rise) and the mixture was stirred at room temperature for 30 minutes, then gradually heated to reflux. The solid went into solution as the color lightened from red to light yellow and potassium bromide separated. After refluxing for 3 hours, the mixture was cooled and most of the ethanol removed on a rotary evaporator. The residue was shaken with 300 ml of ether and 100 ml of water and the layers separated. The aqueous phase was extracted with ether (2×100 ml) and the combined ether layers were washed with 50 ml of water and 50 ml of saturated sodium chloride solution. After drying over magnesium sulfate, the solvent was evaporated to give 66.1 g of a red-orange oil which was fractionated to yield 44.3 g of the title A compound as a yellow oily product, b.p. 163°-166° (0.2 mm). Lit. b.p. 127°-129° (0.05 mm); J. Org. Chem., 37, 1848 (1972).

Workup

  1. customa voluminous yellow-orange precipitate of the potassium salt separated
  2. stirringwas stirred at room temperature for 30 minutes
  3. temperaturegradually heated to reflux
  4. customseparated
  5. temperatureAfter refluxing for 3 hours
  6. temperaturethe mixture was cooled and most of the ethanol
  7. customremoved on a rotary evaporator
  8. stirringThe residue was shaken with 300 ml of ether and 100 ml of water
  9. customthe layers separated
  10. extractionThe aqueous phase was extracted with ether (2×100 ml)
  11. washthe combined ether layers were washed with 50 ml of water and 50 ml of saturated sodium chloride solution
  12. dry with materialAfter drying over magnesium sulfate
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9d965487d5224de1978b5bbb08d93dbd
Source dataset
uspto-grants-1992_05
Patent number
US05116851

Reaction notes

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