Isopropanol → 3-(2,4-Dichlorophenoxy)propanoic acid

HRID 440120Notes

Reaction equation

HRID 440120 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[Cl:14][C:15]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:16]=1[O:17][CH2:18][CH2:19][CH2:20][OH:21].C(O)(C)C>CC(C)=O>[Cl:14][C:15]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:16]=1[O:17][CH2:18][CH2:19][C:20]([OH:3])=[O:21]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 235019(2,4-Dichlorophenoxy)propanolHCID 131709961Jones' reagent

Product 1

HCID 1190483-(2,4-Dichlorophenoxy)propanoic acidYield 91.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent (2.3M, 0.283L, 0.650 mol, CrO3 /H2SO4) is added to a solution of 3-(2,4-dichlorophenoxy)-1-propanol (71.87 g, 0.325 mol) in acetone while maintaining the temperature of the reaction mixture below 40° C. After the addition is complete, isopropanol is added and the reaction mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to give a blue-green solid which is partitioned between ether and water. The organic phase is separated, washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo to obtain the title product as a yellow solid (69.87 g, mp 93°-95° C.).

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture below 40° C
  2. additionAfter the addition
  3. filtrationthe reaction mixture is filtered through diatomaceous earth
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto give a blue-green solid which
  6. customis partitioned between ether and water
  7. customThe organic phase is separated
  8. washwashed with brine
  9. dry with materialdried over anhydrous MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06018a5217134e899a95cf90fb1e8cb7
Source dataset
uspto-grants-1996_05
Patent number
US05516918

Reaction notes

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