Diethyl Ether → Benzene, 1,4-diphenoxy-

HRID 1810609Notes

Reaction equation

HRID 1810609 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-e7aa05b3ad6842ab8c64ba83c6092e6c
Source dataset
uspto-grants-2013_01
Patent number
US08362127B2

Reaction notes

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