2-Chloro-4-hydroxybenzoic acid → (S)-2-methylbutyl 2-chloro-4-hydroxybenzoate

HRID 1761823

反応式

HRID 1761823 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][C@@H:13]([CH2:16][CH3:17])[CH2:14]O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:12][C@@H:13]([CH3:14])[CH2:16][CH3:17])=[O:5]

参加物

5

反応物 2

HCID 918212-Chloro-4-hydroxybenzoic acidHCID 2723602(S)-2-methyl-1-butanol

生成物 1

HCID 14533552(S)-2-methylbutyl 2-chloro-4-hydroxybenzoate収率 98.1%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

実験手順

2-Chloro-4-hydroxybenzoic acid (17.2 g: 100 mmols), 10.5 g (120 mmols) of (S)-2-methylbutanol and 0.17 g (1 mmol) of p-toluenesulfonic acid were refluxed in 100 ml of toluene on heating. Azeotropic water was removed with a Dean Stark trap. After water was no longer distilled off, the residue was left to cool up to room temperature. The resulting product was washed with a sodium bicarbonate aqueous solution until the aqueous phase became alkaline. The product was further washed with water and then with saturated sodium chloride aqueous solution, and dried with anhydrous sodium sulfate. Excess toluene and (S)-2-methylbutanol were mostly distilled off under reduced pressure and the residue was recrystallized from n-hexane to obtain 23.8 g of (S)-2-methylbutyl 2-chloro-4-hydroxybenzoate as a white crystal.

後処理

  1. temperatureon heating
  2. customAzeotropic water was removed with a Dean Stark trap
  3. distillationAfter water was no longer distilled off
  4. waitthe residue was left
  5. washThe resulting product was washed with a sodium bicarbonate aqueous solution until the aqueous phase
  6. washThe product was further washed with water
  7. dry with materialwith saturated sodium chloride aqueous solution, and dried with anhydrous sodium sulfate
  8. distillationExcess toluene and (S)-2-methylbutanol were mostly distilled off under reduced pressure
  9. customthe residue was recrystallized from n-hexane

出典と根拠

ORDレコード
ord-e9e8abbd0ad04f1ea4ccc23168c3344d
出典データセット
uspto-grants-1989_05
特許番号
US04828754

関連ノート

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