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

HRID 1706000Notes

Reaction equation

HRID 1706000 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-5bcfcae8317d4c1585cfca2689ab47a7
Source dataset
uspto-grants-1980_06
Patent number
US04205978

Reaction notes

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