2-氯-4-羟基苯甲酸 → (S)-2-methylbutyl 2-chloro-4-hydroxybenzoate

HRID 1761823

反应方程式

HRID 1761823 反应方程式
[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]

参与物

5

反应物 2

HCID 918212-氯-4-羟基苯甲酸HCID 2723602S-(-)-2-甲基-1-丁醇

产物 1

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

试剂、催化剂与溶剂 2

HCID 6101对甲苯磺酸催化剂HCID 1140甲苯溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-e9e8abbd0ad04f1ea4ccc23168c3344d
来源数据集
uspto-grants-1989_05
专利号
US04828754

关联笔记

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