2,4,5-Trichlorophenol → HCID 23078137, compound

HRID 1374511Notes

Reaction equation

HRID 1374511 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].C([O:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)C>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[O:10][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]([OH:27])=[O:19]

Participants

5

Reactant 3

HCID 72712,4,5-TrichlorophenolHCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 23078137HCID 23078137, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 987 mg (5 mmol) of 2,4,5-trichlorophenol (III) and 1.04 g (7.5 mmol) of anhydrous potassium carbonate were added to 8 ml of anhydrous dimethyl formamide and the mixture was stirred. Then, 1.67 g (7.5 mmol) of 6-bromohexanoic acid ethyl ester was added thereto, and the mixture was stirred at 60° C. for 16 hours. After the reaction was completed, the solvent was concentrated under reduced pressure. The residue was extracted with dichloromethane, washed with water, and was then concentrated under reduced pressure to dryness. The residue was dissolved in a mixed solution of 10 ml of dioxane and 12.5 ml of methanol, and 2.5 ml of 10 N sodium hydroxide was added thereto with stirring. The mixture was stirred at room temperature for 6 hours. After the reaction was completed, 5 ml of water was added to the mixture and neutralized with 6 N hydrochloric acid. The solvent was evaporated under reduced pressure to dryness, 1 N hydrochloric acid was added to the residue and the residue was extracted with chloroform. After washing with water, the residue was concentrated under reduced pressure to dryness and was powdered using a mixed solution of hexane and ether to obtain 6-(2,4,5-trichlorophenoxy) hexanoic acid (Ia) (hereinafter, referred to as “compound (Ia)”) in an amount of 1.32 g (yield: 85%).

Workup

  1. stirringthe mixture was stirred at 60° C. for 16 hours
  2. concentrationthe solvent was concentrated under reduced pressure
  3. extractionThe residue was extracted with dichloromethane
  4. washwashed with water
  5. concentrationwas then concentrated under reduced pressure to dryness
  6. dissolutionThe residue was dissolved in a mixed solution of 10 ml of dioxane and 12.5 ml of methanol, and 2.5 ml of 10 N sodium hydroxide
  7. additionwas added
  8. stirringwith stirring
  9. stirringThe mixture was stirred at room temperature for 6 hours
  10. addition5 ml of water was added to the mixture and neutralized with 6 N hydrochloric acid
  11. customThe solvent was evaporated under reduced pressure to dryness, 1 N hydrochloric acid
  12. additionwas added to the residue
  13. extractionthe residue was extracted with chloroform
  14. washAfter washing with water
  15. concentrationthe residue was concentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-447dc8635cda4302a2e2a377e676c1c7
Source dataset
uspto-grants-2007_01
Patent number
US07166440B2

Reaction notes

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