Hydrochloric Acid → 4-Chloro-5-(4-chlorophenoxy)-2-nitrobenzoic Acid

HRID 2073943

Reaction equation

HRID 2073943 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[Cl:11][C:12]1[C:20](Cl)=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=1.Cl>COCCOCCOC>[Cl:11][C:12]1[C:20]([O:10][C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 46844-ChlorophenolHCID 24758Sodium hydrideHCID 5836424,5-Dichloro-2-nitrobenzoic acid

Product 1

HCID 142334244-Chloro-5-(4-chlorophenoxy)-2-nitrobenzoic Acid

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent3×

Conditions

Temperature
10 °C

Procedure

To 30 ml of dry diglyme under a nitrogen atmosphere was added 0.960 g (0.02 mol) of sodium hydride dispersion in mineral oil (50%). The solution was cooled to 10° C. and 1.28 g (0.01M) 4-chlorophenol in 15 ml of dry diglyme was added dropwise while maintaining the temperature at 10° C. This was followed by the dropwise addition of 2.36 g (0.01 mol) of 4,5-dichloro-2-nitrobenzoic acid in 15 ml of dry diglyme. The reaction mixture was then heated to 153° C. (oil bath) for 1 hour and 45 minutes. The reaction mixture was cooled to room temperature and poured into an ice/water mixture. The pH was then adjusted to 1.5 with 6N hydrochloric acid. The solution was extracted with ethyl acetate, and the organic layer dried over anhydrous magnesium sulfate. The solvent was removed and the crude solid triturated with hexane, followed by recrystallization from carbon tetrachloride to give the title compound: yield 1.65 g (50%) m.p. 160°-162° C.

Workup

  1. temperaturewhile maintaining the temperature at 10° C
  2. temperatureThe reaction mixture was then heated to 153° C. (oil bath) for 1 hour
  3. custom45 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionThe solution was extracted with ethyl acetate
  6. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  7. customThe solvent was removed
  8. customthe crude solid triturated with hexane
  9. customfollowed by recrystallization from carbon tetrachloride

Sources & evidence

ORD record
ord-bab2a9a8b5134cea8cbc39142bdae17b
Source dataset
uspto-grants-1990_04
Patent number
US04920224

Linked notes

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