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

HRID 2423595Notes

Reaction equation

HRID 2423595 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>[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:13][CH:12]=1)([O-:10])=[O:9]

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-e5803457e1bc43d2a17dd502c3bcc4f9
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

Loading…