Diethyl Ether → Benzene, 1,4-diphenoxy-

HRID 1808260Notes

Reaction equation

HRID 1808260 reaction equation
CCOCC.[O:6]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[K+].Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.C1(C)C=CC=CC=1>[O:6]([C:13]1[CH:14]=[CH:15][C:16]([O:19][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7961BromobenzeneHCID 132544-PhenoxyphenolHCID 14797Potassium Hydroxide

Product 1

HCID 520487Benzene, 1,4-diphenoxy-

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
153 °C

Procedure

1,4-diphenoxybenzene is prepared by the Ullmann ether synthesis as follows. 4-Phenoxyphenol (186.2 g, 1.0 mol) is dissolved in 1600 g of DMF with 300 mL toluene under nitrogen. A 50% KOH solution (112.0 g, 1.0 mol) is added followed by azeotropic removal of the water and stripping of the toluene. Bromobenzene (157.0 g, 1.0 mol) and cupric oxide (3.2 g, 0.04 mol) are then added and the reaction solution held at reflux (153° C.) for 24 hr. The DMF is then removed by stripping and the residue worked up to give 1,4-diphenoxybenzene

Workup

  1. customfollowed by azeotropic removal of the water and stripping of the toluene
  2. customThe DMF is then removed

Sources & evidence

ORD record
ord-60bba4ae17a14ec1bfc856f78bb9ebae
Source dataset
uspto-grants-2013_01
Patent number
US08357738B2

Reaction notes

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