4-Chlorophenol → HCID 578694, compound

HRID 839294Notes

Reaction equation

HRID 839294 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[OH-].[Na+]>O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 5238Sodium IodideHCID 83742-Chlorobenzoic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 578694HCID 578694, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a well stirred mixture of 15.7 g. (0.1 mole) of 2-chlorobenzoic acid and 15.0 g. (0.1 mole) of sodium iodide in 250 ml. of 4-chlorophenol was rapidly added a solution of 16 g. (0.4 mole) of sodium hydroxide dissolved in 16 ml. of water. The reaction mixture was heated and concentrated under reduced pressure to an internal temperature of about 145° C. to remove the water and excess 4-chlorophenol. The residue was then stirred at 170° C. for about 7 hours, cooled and diluted with 250 ml. of water. The aqueous solution was extracted with ethyl acetate after acidifying with dilute hydrochloric acid. The ethyl acetate extractions were washed with water, dried and concentrated under reduced pressure. The residue was recrystallized from a benzene-hexane mixture to give pure 2-(4'-chlorophenoxy)benzoic acid, m.p. 114°-115° C.

Workup

  1. additionmixture of 15.7 g
  2. temperatureThe reaction mixture was heated
  3. concentrationconcentrated under reduced pressure to an internal temperature of about 145° C.
  4. customto remove the water and excess 4-chlorophenol
  5. stirringThe residue was then stirred at 170° C. for about 7 hours
  6. temperaturecooled
  7. additiondiluted with 250 ml
  8. extractionThe aqueous solution was extracted with ethyl acetate
  9. extractionThe ethyl acetate extractions
  10. washwere washed with water
  11. customdried
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-13d8d6e8f6784a51830e69f40db4ae85
Source dataset
uspto-grants-1978_06
Patent number
US04094900

Reaction notes

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