Potassium Carbonate → 4-Acetylamino-2-hexyloxybenzoic acid methyl ester

HRID 1608230Notes

Reaction equation

HRID 1608230 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[CH:7][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:9][CH:10]=1)[OH:6].[CH2:16](I)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:5]=1[O:6][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 125271-IodohexaneHCID 77719Methyl 4-acetamidosalicylate

Product 1

HCID 543827224-Acetylamino-2-hexyloxybenzoic acid methyl esterYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of p-acetylaminosalicylic acid methyl ester (5.0 g), hexyl iodide (7.6 g), potassium carbonate (9.9 g), and dimethylformamide (20 ml) is stirred at 70° C. for 30 hours. The reaction mixture is poured into ice-water and extracted with diethyl ether. The organic layer is washed successively with aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated. The residue is chromatographed on silica gel with chloroform-methanol (20:1) to give 4-acetylamino-2-hexyloxybenzoic acid methyl ester (4.9 g) as an oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer is washed successively with aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on silica gel with chloroform-methanol (20:1)

Sources & evidence

ORD record
ord-665c0c6934924b94b53cfcc198c4c414
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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