Hydrochloric Acid → HCID 17816559, compound

HRID 2249681Notes

Reaction equation

HRID 2249681 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[OH:16])[C:10]([OH:12])=[O:11])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:24](OC(=O)C)(=[O:26])[CH3:25].Cl>CN(C)C=O.O.C(OCC)(=O)C>[C:24]([O:16][C:15]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:17])(=[O:26])[CH3:25]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 17816469HCID 17816469, compound

Product 1

HCID 17816559HCID 17816559, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 75 ml of N,N-dimethylformamide are suspended 7.5 g of 3-(3-ethoxy-3-oxopropyl)-4-hydroxybenzoic acid, 17.5 g of potassium carbonate and 7.4 ml of acetic anhydride. The mixture thus obtained is stirred at ambient temperature for 2 hours. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 1.8 g of 4-(acetyloxy)-3-(3-ethoxy-3-oxopropyl)benzoic acid as a light brown-colored solid product.

Workup

  1. customThe mixture thus obtained
  2. customthe organic layer is separated
  3. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-ab5eb2139198434ca5ca2329f072b6b8
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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