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

HRID 2166001

Reaktionsgleichung

Reaktionsgleichung von HRID 2166001
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 14533552(S)-2-methylbutyl 2-chloro-4-hydroxybenzoateAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-53495a0a18e84d6bbcc4e408a88f11fa
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04943386

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