1,2-Dichloro-4-nitrobenzene → Methyl 2-[4-(2-chloro-4-nitrophenoxy)phenoxy]propanoate

HRID 2419498Notes

Reaction equation

HRID 2419498 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1.[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1Cl>CS(C)=O>[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl ester

Product 1

HCID 12883848Methyl 2-[4-(2-chloro-4-nitrophenoxy)phenoxy]propanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6.5 g of pulverised potassium hydroxide and 20 g of methyl 4-hydroxy-α-phenoxypropionate in 250 ml of dry dimethyl sulphoxide are charged at 0° C into a three-necked flask. With stirring, and at a temperature between 0° and 5° C, 19.5 g of 3,4-dichloro-nitrobenzene are added by small amounts and stirring is continued for 12 hours at room temperature. Thereafter the reaction mixture is poured into ice-water and extracted with ethyl acetate. The extract is dried over sodium sulphate and the solvent distilled off to yield an oily product which is then subjected to high vacuum distillation. The resultant substance, viz. methyl 4-(2'-chloro-4'-nitrophenoxy)-α-phenoxypropionate (yield 27 g), boils at 194° C/0.01 Torr (compound 1).

Workup

  1. stirringstirring
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract is dried over sodium sulphate
  4. distillationthe solvent distilled off
  5. customto yield an oily product which
  6. distillationis then subjected to high vacuum distillation

Sources & evidence

ORD record
ord-4f2640b31cef42d59a4b577c69368406
Source dataset
uspto-grants-1978_08
Patent number
US04106925

Reaction notes

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