Phenol → Benzene, 1-nitro-4-(phenoxymethyl)-

HRID 1950023Notes

Reaction equation

HRID 1950023 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[CH:13][CH:12]=1)([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>C(OCC)(=O)C>[C:1]1([O:7][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 99674Benzene, 1-nitro-4-(phenoxymethyl)-Yield 90.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of phenol (11.3 g), 4-nitrobenzyl bromide (25.9 g), potassium carbonate (16.6 g) and methyl ethyl ketone (100 ml) was stirred for 15.5 hours at 80° C. Ethyl acetate was added thereto, the insoluble material was removed by filtration, the solvent was evaporated in vacuo, and the resulting residue was recrystallized from hexane-ethyl acetate to provide the title compound (pale yellow powder) (24.9 g).

Workup

  1. customthe insoluble material was removed by filtration
  2. customthe solvent was evaporated in vacuo
  3. customthe resulting residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-08a2ee5bc2954f78a605cb73ef8512a0
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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