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

HRID 1720160노트

반응식

HRID 1720160 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-58f7e628e8ac40db84ba656c5c963cf0
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05504244

반응 노트

불러오는 중…