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

HRID 986697Notes

Reaction equation

HRID 986697 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[Br:22])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2].[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([O:28][C:5]1[C:6]([CH2:25][CH2:26][CH3:27])=[C:7]([CH:23]=[CH:24][C:4]=1[C:1](=[O:3])[CH3:2])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[Br:22])(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13338867HCID 13338867, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a mixture of pyridine (10 ml) and acetic anhydride (10 ml) was dissolved 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoic acid (2 g). The solution was heated at 100° to 120° C. for 14 hours, which was then concentrated. The residue was dissolved in chloroform. The solution was washed with dilute hydrochloride acid, which was then dried on sodium sulfate. From the resultant was removed the solvent by evaporation, and the residue was chromatographed on a column of silica gel. Elution was conducted with hexane-ethyl acetate (3:1), (2:1), (1:1) and ethyl acetate in that order. Ethyl acetate fractions were combined and concentrated. The residue was crystallized from chloroform-hexane to give 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoic acid (1.0 g), m.p. 155°-156° C.

Workup

  1. temperatureThe solution was heated at 100° to 120° C. for 14 hours
  2. concentrationwhich was then concentrated
  3. dissolutionThe residue was dissolved in chloroform
  4. washThe solution was washed with dilute hydrochloride acid, which
  5. customwas then dried on sodium sulfate
  6. customFrom the resultant was removed the solvent
  7. customby evaporation
  8. customthe residue was chromatographed on a column of silica gel
  9. washElution
  10. concentrationconcentrated
  11. customThe residue was crystallized from chloroform-hexane

Sources & evidence

ORD record
ord-732ff6876d04499a85438c2731c1d17d
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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