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

HRID 1262974

反応式

HRID 1262974 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-d1d2494460a54e949443536b26301acf
出典データセット
uspto-grants-1984_06
特許番号
US04454340

関連ノート

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