Chromic Acid → HCID 15058687, compound

HRID 1087896Notes

Reaction equation

HRID 1087896 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH2:14][CH2:15][F:16])=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8].[Cr](O)(O)(=O)=[O:18]>CC(C)=O.Cl>[F:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH2:14][CH2:15][F:16])=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]([OH:18])=[O:8]

Participants

5

Reactant 2

HCID 24425Chromic AcidHCID 15058684HCID 15058684, compound

Product 1

HCID 15058687HCID 15058687, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred solution of 3.0 grams (0.013 mole) of 2,3-di(2-fluoroethoxy)benzaldehyde in 10 ml of acetone was added 4.9 ml of a 2.6 M solution of aqueous chromic acid in acetone (Jones' reagent). The mixture was stirred at room temperature for 30 minutes, and the solvent was removed by evaporation under reduced pressure leaving a residue. This residue was dissolved in 30 ml of 1 N hydrochloric acid, and the acidic solution was extracted with five 30 ml portions of diethyl ether. The combined organic phase was extracted with three 35 ml portions of an aqueous, 10% sodium hydroxide solution. The basic extracts were combined and acidified. The acidic solution was extracted with five 30 ml portions of diethyl ether. The extracts were combined and washed with two 25 ml portion of an aqueous, saturated sodium chloride solution. The washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving a solid residue. This solid was recrystallized from toluene to yield 1.4 gram of 2,3-di(2-fluoroethoxy)benzoic acid, mp 104°-105° C.

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. customleaving a residue
  3. extractionthe acidic solution was extracted with five 30 ml portions of diethyl ether
  4. extractionThe combined organic phase was extracted with three 35 ml portions of an aqueous, 10% sodium hydroxide solution
  5. extractionThe acidic solution was extracted with five 30 ml portions of diethyl ether
  6. washwashed with two 25 ml portion of an aqueous, saturated sodium chloride solution
  7. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure
  10. customleaving a solid residue
  11. customThis solid was recrystallized from toluene

Sources & evidence

ORD record
ord-1e55cc99de8f4900a560cd101662ce1b
Source dataset
uspto-grants-1990_10
Patent number
US04960884

Reaction notes

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