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

HRID 1761823

Reaction equation

HRID 1761823 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e9e8abbd0ad04f1ea4ccc23168c3344d
Source dataset
uspto-grants-1989_05
Patent number
US04828754

Linked notes

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