Acetic Acid → 4-[3-(3-Acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoic acid

HRID 986708Notes

Reaction equation

HRID 986708 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH2:28][CH2:29][CH3:30])=[C:7]([CH:22]=[CH:23][C:24]=1[C:25](=[O:27])[CH3:26])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[Br:21])(=[O:3])[CH3:2].C(O)(=[O:33])C.[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O>[C:1]([O:4][C:5]1[C:6]([CH2:28][CH2:29][CH3:30])=[C:7]([CH:22]=[CH:23][C:24]=1[C:25](=[O:27])[CH3:26])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]([OH:33])=[O:18])=[CH:15][C:14]=1[Br:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 20157039HCID 20157039, compound

Product 1

HCID 137456304-[3-(3-Acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]3-bromobenzaldehyde (2.39 g) in acetone (50 ml) was added acetic acid (50 ml). To the well stirred mixture was added pulverized potassium permanganate (1.58 g) by portions at room temperature. The reaction was allowed to proceed while stirring for one hours. The reaction mixture was concentrated under reduced pressure, and the concentrate was subjected to extraction with chloroform. Insoluble materials were filtered off, and the filtrate was washed with a dilute aqueous solution of hydrogen peroxide, then with water. The resulting solution was dried and concentrated to give colorless and clear syrup. Crystallization from aqueous alcohol gave 4-[3-(3-acetoxy-4-acetyl-2 propylphenoxy)propoxy]-3-bromobenzoic acid (2.0 g), m.p. 155°-156° C.

Workup

  1. additionwas added
  2. customat room temperature
  3. stirringwhile stirring for one hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionthe concentrate was subjected to extraction with chloroform
  6. filtrationInsoluble materials were filtered off
  7. washthe filtrate was washed with a dilute aqueous solution of hydrogen peroxide
  8. customThe resulting solution was dried
  9. concentrationconcentrated
  10. customto give colorless
  11. customCrystallization from aqueous alcohol

Sources & evidence

ORD record
ord-cfaa9183f3f34940be5da01a2ec97ab9
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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