Hydrochloric Acid → 3-(4-Butoxy-2-methoxybenzoyl)benzoic acid

HRID 1720160Notes

Reaction equation

HRID 1720160 reaction equation
[CH2:1]([O:5][C:6]1[CH:22]=[CH:21][C:9]([C:10]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])=[O:11])=[C:8]([OH:23])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:24]I.Cl>[OH-].[Na+].C(O)C.O>[CH2:1]([O:5][C:6]1[CH:22]=[CH:21][C:9]([C:10]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])=[O:11])=[C:8]([O:23][CH3:24])[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 224203853-(4-Butoxy-2-hydroxybenzoyl)benzoic acid

Product 1

HCID 224203803-(4-Butoxy-2-methoxybenzoyl)benzoic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(4-butoxy-2-hydroxybenzoyl)benzoic acid (0.85 g), prepared as described in Example 26, is heated under reflux in a mixture of 2N sodium hydroxide (2.8 ml) and ethanol (10 ml) for 30 minutes. The reaction mixture is then cooled to 60° C. and methyl iodide (10 ml) is added. The resulting mixture was heated at 60° for 72 hours, cooled, acidified with concentrated hydrochloric acid and diluted with water (100 ml). The product is extracted with ether (3×25 ml). The extracts are dried over magnesium sulfate, filtered and evaporated to dryness. 2N Sodium hydroxide (2 ml) is added to the residue and the mixture heated under reflux for 6 hours. The reaction mixture is acidified with concentrated hydrochloric acid, diluted with water (100 ml), and extracted with ether (3×25 ml). The residue is chromatographed on silica (hexane:ether:acetic acid at 90:10:1) to yield 3-(4-butoxy-2-methoxybenzoyl)benzoic acid (0.46 g), m.p. 144°-145° C.

Workup

  1. temperatureis heated
  2. temperatureThe resulting mixture was heated at 60° for 72 hours
  3. temperaturecooled
  4. extractionThe product is extracted with ether (3×25 ml)
  5. dry with materialThe extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. addition2N Sodium hydroxide (2 ml) is added to the residue
  9. temperaturethe mixture heated
  10. temperatureunder reflux for 6 hours
  11. additiondiluted with water (100 ml)
  12. extractionextracted with ether (3×25 ml)
  13. customThe residue is chromatographed on silica (hexane:ether:acetic acid at 90:10:1)

Sources & evidence

ORD record
ord-58f7e628e8ac40db84ba656c5c963cf0
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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