Hydrochloric Acid → Benzoic acid, 2-hydroxy-4-methoxy-, phenyl ester

HRID 1262974

반응식

HRID 1262974 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16].Cl>O.C(Cl)Cl>[OH:9][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 90073-MethoxyphenolHCID 15891Phenyl chloroformateHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 11436480Benzoic acid, 2-hydroxy-4-methoxy-, phenyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a 1,000-mL, three-neck, nitrogen-purged flask was added 26.5 g (0.21 mole) of 3-methoxyphenol, 215 mL of methylene chloride, 32 g (0.24 mole) of aluminum chloride and 32 mL (0.26 mole) of phenyl chloroformate. This mixture was heated to reflux. After 24 hours, the mixture was cooled to 20°-30° C. and 400 mL of water and 32 mL of 37% hydrochloric acid were added. The layers were separated and the organic layer washed with two 100-mL portions of 5N hydrochloric acid. The organic layer was dried with anhydrous magnesium sulfate, filtered, then the solvent stripped off under vacuum. The crude product was recrystallized from heptane. The yield of phenyl 2-hydroxy-4-methoxybenzoate (white, m.p. 61.5°-62.5° C.) obtained was 49%.

후처리

  1. customTo a 1,000-mL, three-neck, nitrogen-purged flask
  2. temperatureThis mixture was heated to reflux
  3. temperaturethe mixture was cooled to 20°-30° C.
  4. customThe layers were separated
  5. washthe organic layer washed with two 100-mL portions of 5N hydrochloric acid
  6. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe crude product was recrystallized from heptane

출처 및 근거

ORD 기록
ord-d1d2494460a54e949443536b26301acf
출처 데이터셋
uspto-grants-1984_06
특허 번호
US04454340

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