Acetic Acid → 2-(5-Chloro-2-phenoxyphenyl)acetic acid

HRID 1448462Notes

Reaction equation

HRID 1448462 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:6](CC(N2CCOCC2)=S)[CH:7]=1.[C:24]([OH:27])(=[O:26])[CH3:25].O.S(=O)(=O)(O)O>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:6]([CH2:25][C:24]([OH:27])=[O:26])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 127651112-(5-Chloro-2-phenoxyphenyl)-1-morpholinoethanethione

Product 1

HCID 127651142-(5-Chloro-2-phenoxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To this morpholine residue is added 290 ml of glacial acetic acid, 61 ml of water and 87 ml of sulfuric acid (96%), and the mixture refluxed for a period of 21 hours. On cooling, the reaction mixture is dissolved in ethyl ether, washed with water until the water wash appears neutral and extracted with a 10% sodium carbonate solution. The aqueous alkaline layer is acidified with a 2 N solution of hydrochloric acid and re-extracted into diethyl ether. The ether solution is washed with water until the water washings are neutral, dried over anhydrous sodium sulfate and filtered. The solvent is removed by distillation from the filtrate and the remaining residue is crystallized from cyclohexane to yield 30.5 grams of (5-chloro-2-phenoxyphenyl)acetic acid having a m.p. of 119°-123° C.

Workup

  1. temperaturethe mixture refluxed for a period of 21 hours
  2. temperatureOn cooling
  3. washwashed with water until the water
  4. washwash
  5. extractionextracted with a 10% sodium carbonate solution
  6. extractionre-extracted into diethyl ether
  7. washThe ether solution is washed with water until the water washings
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solvent is removed by distillation from the filtrate
  11. customthe remaining residue is crystallized from cyclohexane

Sources & evidence

ORD record
ord-2e91b197024148eb809890fb6a4eb552
Source dataset
uspto-grants-1979_12
Patent number
US04180559

Reaction notes

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