Acetic Acid → 4-(S)-isopropyl-2-methyloxazoline

HRID 2184173Notes

Reaction equation

HRID 2184173 reaction equation
[NH2:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:5])[CH3:4].[C:8](O)(=O)[CH3:9].O>C1(C)C=CC=CC=1>[CH:3]([C@H:2]1[CH2:6][O:7][C:8]([CH3:9])=[N:1]1)([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 640993L-Valinol

Product 1

HCID 69323254-(S)-isopropyl-2-methyloxazolineYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 g (0.194 mol) valinol are dissolved with 11.64 g (0.194 mol) acetic acid in 60 ml toluol and cooked for 24 h under reflux in the water separator. After cooling the solution is extracted with 10% hydrochloric acid. The aqueous phase is neutralized with 40% sodium hydroxide solution and extracted with diethyl ether. The organic phase is dried via Na2SO4 and the solvent removed. Distillation (112° C.) produces 19.2 g (78%) 4-(S)-isopropyl-2-methyloxazoline as a colourless oil.

Workup

  1. temperatureAfter cooling the solution
  2. extractionis extracted with 10% hydrochloric acid
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic phase is dried via Na2SO4
  5. customthe solvent removed
  6. distillationDistillation (112° C.)

Sources & evidence

ORD record
ord-14e7f6b184564bf7807ad9a1b0c4c348
Source dataset
uspto-grants-2005_05
Patent number
US06900313B2

Reaction notes

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