4-Chlorophenol → Methyl 2-[4-(4-Chlorophenoxy-methyl)-phenoxy]-propionate

HRID 426435Notes

Reaction equation

HRID 426435 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][C:11]1[CH:23]=[CH:22][C:14]([O:15][CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=1.[Na]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][C:11]2[CH:23]=[CH:22][C:14]([O:15][CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 5360545SodiumHCID 18981037Methyl 2-(4-chloromethylphenoxy)propionate

Product 1

HCID 19834514Methyl 2-[4-(4-Chlorophenoxy-methyl)-phenoxy]-propionateYield 77.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.7 gm (0.044 mol) of 4-chloro-phenol and 10 gm (0.044 mol) of methyl 2-(4-chloromethyl-phenoxy)-propionate were added to a solution of 1.01 gm of sodium in 80 ml of ethanol, and the resulting mixture was refluxed for 6 hours, while stirring. Thereafter, the solvent was removed in vacuo, the residue was admixed with water, and the aqueous mixture was extracted with ether. The ethereal extract solution was washed with 1 N potassium hydroxide and then with water, dried and evaporated, leaving 11 gm of an oily residue which was purified by passing it through a silicagel column with benzene as the flow agent. The initially oily product crystallized upon standing and then had a melting point of 76° C.; it was identified to be the compound of the formula ##STR18##

Workup

  1. temperaturethe resulting mixture was refluxed for 6 hours
  2. customThereafter, the solvent was removed in vacuo
  3. extractionthe aqueous mixture was extracted with ether
  4. extractionThe ethereal extract solution
  5. washwas washed with 1 N potassium hydroxide
  6. dry with materialwith water, dried
  7. customevaporated

Sources & evidence

ORD record
ord-0091b73aa5bf4650a3b0cf61ecbc839e
Source dataset
uspto-grants-1979_10
Patent number
US04169720

Reaction notes

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