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

HRID 986710Notes

Reaction equation

HRID 986710 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH2:33][CH2:34][CH3:35])=[C:7]([CH:27]=[CH:28][C:29]=1[C:30](=[O:32])[CH3:31])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:25]=[CH:24][C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[CH:15][C:14]=1[Br:26])(=[O:3])[CH3:2].Cl>O1CCOCC1>[C:1]([O:4][C:5]1[C:6]([CH2:33][CH2:34][CH3:35])=[C:7]([CH:27]=[CH:28][C:29]=1[C:30](=[O:32])[CH3:31])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:25]=[CH:24][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[Br:26])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 20157030Tert-butyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate

Product 1

HCID 137456304-[3-(3-Acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoic acidYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
20 °C

Procedure

In 10 ml of dioxane was dissolved 1.5 g of tert-butyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate. To the solution was added under stirring at 20° C., 10 ml of a dioxane solution (2 N) of hydrogen chloride which was previously ice-cooled. The mixture was further stirred for 30 minutes at room temperature, and then to the mixture was added 10 ml of the dioxane solution of hydrogen chloride. The mixture was stirred for 1.5 hours, and concentrated urder reduced pressure. The resultant was dissolved in 30 ml of chloroform, and the solution was washed with 30 ml of water and then dried over with magnesium sulfate. Chloroform was removed by evaporation under reduced pressure, and the resultant was dissolved in isopropyl ether. The solution was subjected to a treatment using activated charcoal, and to the solution was added hexane for crystallization. The crystals were collected by filtration, subjected to purification by silica gel column chromatography, and then recrystallized from aqueous ethanol to give 0.35 g of 4-[3-(3-acetoxy-4-acetyl 2-propylphenoxy)propoxy]-3-bromobenzoic acid as colorless crystals. m.p. 154°-156° C.

Workup

  1. additionTo the solution was added
  2. temperaturecooled
  3. stirringThe mixture was further stirred for 30 minutes at room temperature
  4. stirringThe mixture was stirred for 1.5 hours
  5. concentrationconcentrated urder reduced pressure
  6. dissolutionThe resultant was dissolved in 30 ml of chloroform
  7. washthe solution was washed with 30 ml of water
  8. dry with materialdried over with magnesium sulfate
  9. customChloroform was removed by evaporation under reduced pressure
  10. dissolutionthe resultant was dissolved in isopropyl ether
  11. additionto the solution was added hexane
  12. customfor crystallization
  13. filtrationThe crystals were collected by filtration
  14. customsubjected to purification by silica gel column chromatography
  15. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-659df72cab95405aaef97b884628399f
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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