Water → Benzene, 1,4-bis[(2-chloro-4-methoxyphenoxy)methyl]-

HRID 744173Notes

Reaction equation

HRID 744173 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].[OH-:11].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=1.O.CN([CH:27]=[O:28])C>>[C:18]1([CH2:21][O:11][C:3]2[CH:4]=[CH:5][C:6]([O:28][CH3:27])=[CH:7][C:2]=2[Cl:1])[CH:19]=[CH:20][C:15]([CH2:14][O:10][C:3]2[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=2[Cl:1])=[CH:16][CH:17]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 693351,4-Bis(bromomethyl)benzeneHCID 874592-Chloro-4-methoxyphenol

Product 1

HCID 510413Benzene, 1,4-bis[(2-chloro-4-methoxyphenoxy)methyl]-

Procedure

To a stirred mixture of 10.0 g of 2-chloro-4-methoxyphenol and 2.5 g of NaOH in 50 mL of DMF add 7.0 g of α, α'-dibromo-p-xylene and stir the so-formed reaction mixture at room temperature for 4 hrs. Add 300 mL of water and filter the crude precipitated solid. Purify the crude product by re-crystallization from the methylene chloride to produce 9.12 g of 1,1'-[1,4-phenylene bis(methylenoxy)]-bis [2-chloro-4methoxybenzene] as a pure compound.

Workup

  1. customthe so-formed reaction mixture at room temperature for 4 hrs
  2. filtrationfilter the crude
  3. customprecipitated solid
  4. customPurify the crude product
  5. customby re-crystallization from the methylene chloride

Sources & evidence

ORD record
ord-349919a0dab44caaa00fb9636c03cf8c
Source dataset
uspto-grants-1996_09
Patent number
US05559133

Reaction notes

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