Fenteracol → 2-(2,4,5-Trichloro-phenoxy)-ethyl 2-[4-(4-chlorophenoxymethyl)-phenoxy]-propionate

HRID 426438Notes

Reaction equation

HRID 426438 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][C:8]2[CH:20]=[CH:19][C:11]([O:12][CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:33]=[C:32]([Cl:34])[C:31]([Cl:35])=[CH:30][C:25]=1[O:26][CH2:27]CO.[Na]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[CH:20]=[CH:19][C:11]([O:12][CH:13]([CH3:18])[C:14]([O:16][CH2:17][CH2:27][O:26][C:25]3[CH:30]=[C:31]([Cl:35])[C:32]([Cl:34])=[CH:33][C:24]=3[Cl:23])=[O:15])=[CH:10][CH:9]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 16462FenteracolHCID 5360545SodiumHCID 19834514Methyl 2-[4-(4-Chlorophenoxy-methyl)-phenoxy]-propionate

Product 1

HCID 538539382-(2,4,5-Trichloro-phenoxy)-ethyl 2-[4-(4-chlorophenoxymethyl)-phenoxy]-propionate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture consisting of 2.2 gm of methyl 2-[4-(4-chlorophenoxy-methyl)-phenoxy]-propionate, 2.4 gm of 2-(2,4,5-trichloro-phenoxy)-ethanol and 0.03 gm of sodium was heated at about 120°-150° C. and a pressure of 150 mm Hg for four hours. After cooling, the reaction mixture was briefly boiled with acetone, the cooled solution was filtered, and the solvent was removed from the filtrate in vacuo. The residue was recrystallized from ethanol/water, yielding 1.3 gm (36% of theory) of the compound of the formula ##STR19## which had a melting point of 83° C.

Workup

  1. temperaturewas heated at about 120°-150° C.
  2. temperatureAfter cooling
  3. filtrationthe cooled solution was filtered
  4. customthe solvent was removed from the filtrate in vacuo
  5. customThe residue was recrystallized from ethanol/water
  6. customyielding 1.3 gm (36% of theory) of the compound of the formula ##STR19## which

Sources & evidence

ORD record
ord-fac85202ceaa4c29acd8b6831978d813
Source dataset
uspto-grants-1979_10
Patent number
US04169720

Reaction notes

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