Sodium Hydroxide → HCID 67578202, compound

HRID 744174Notes

Reaction equation

HRID 744174 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][Br:20])=[CH:15][CH:14]=1.[OH-:21].[Na+]>CN(C=O)C>[Br:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:10][C:3]2([O:21][C:3]3([O:10][CH2:12][C:13]4[CH:18]=[CH:17][C:16]([CH2:19][Br:20])=[CH:15][CH:14]=4)[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][CH:2]3[Cl:1])[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][CH:2]2[Cl:1])=[CH:14][CH:15]=1

Participants

5

Reactant 3

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

Product 1

HCID 67578202HCID 67578202, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 5 g of 2-chloro-4-methoxyphenol to a mixture of 17 g of α,α'-dibromo-p-xylene to a stirred mixture of 2.5 g of 50:50 (w/w) NaOH:H20 and 50 mL of DMF. Stir the so-formed mixture for 4 hours. Partition the reaction mixture with methylene chloride and water. Separate the organic layer and remove the solvent by rotary evaporation to obtain a solid residue. Purify the residue on a silica gel chromatography column using pure hexane to pure methylene chloride as the eluants to provide 8 g of 1-[4-bromomethylbenzyloxy]-2-chloro-4methoxyphenyl ether.

Workup

  1. customPartition the reaction mixture with methylene chloride and water
  2. customSeparate the organic layer
  3. customremove the solvent
  4. customby rotary evaporation
  5. customto obtain a solid residue
  6. customPurify the residue on a silica gel chromatography column

Sources & evidence

ORD record
ord-936152f2943d4a70a9140ee72cf15b13
Source dataset
uspto-grants-1996_09
Patent number
US05559133

Reaction notes

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