Sodium Hydroxide → HCID 13338867, compound

HRID 1285396Notes

Reaction equation

HRID 1285396 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][C:14]=2[Br:24])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[Br:24])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13338863Ethyl 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-bromobenzoate

Product 1

HCID 13338867HCID 13338867, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-bromobenzoate (1.50 g), ethanol (15 ml) and 1N sodium hydroxide (10 ml) was refluxed for 0.5 hour, then concentrated, acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and dried over sodium sulfate, the solvent was distilled off, and the residue was chromatographed on a column of silica gel (50 g), and eluted with a solution of chloroform-acetone-formic acid (9:1:0.1). Recrystallization from ethyl acetate gave 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-bromobenzoic acid as colorless needles (1.06 g). Melting point 180°-182° C.

Workup

  1. temperaturewas refluxed for 0.5 hour
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe residue was chromatographed on a column of silica gel (50 g)
  8. washeluted with a solution of chloroform-acetone-formic acid (9:1:0.1)
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-75f04f5dcca04340a853302afe1f1996
Source dataset
uspto-grants-1986_01
Patent number
US04567201

Reaction notes

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