4-Chlorophenol → HCID 12531879, compound

HRID 1863315Notes

Reaction equation

HRID 1863315 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 10942334Sodium MethoxideHCID 20392602HCID 20392602, compound

Product 1

HCID 12531879HCID 12531879, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1.38 g of p-chlorophenol and 0.585 g of sodium methoxide in 10 ml of methanol is added a solution of 3.53 g of methyl α-bromo-α-[p-(p-methylsulfonylphenoxy)phenyl]acetate in 15 ml of methanol. The mixture is refluxed for 20 hours, chilled and filtered to give 2.71 g of white crystals, mp 182°-183° C. Recrystallization by heating in 75 ml of acetone and adding 20 ml of dichloromethane, followed by adding hexane gives on chilling the product as white crystals, mp 182°-183° C.

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. temperaturechilled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f014f26e263343baaa309d5adb987d33
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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