Isopropanol → Isopropyl 2-pyridylacetate

HRID 2352576Notes

Reaction equation

HRID 2352576 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].C(=O)(O)[O-].[Na+].[CH3:17][CH:18](O)[CH3:19]>Cl>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH:18]([CH3:19])[CH3:17])=[O:10]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 14649611Isopropyl 2-pyridylacetate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a solution of 355 mg of 2-pyridylacetic acid hydrochloride in 5 ml of 2-propanol, hydrogen chloride was saturated at 0° C., and the solution was stirred for 10 hours at room temperature. Sodium bicarbonate was added to the reaction mixture to make alkaline, and the solution was extracted with 50 ml of diethyl ether. The ethereal layer was washed successively with water and a suturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 305 mg of isopropyl 2-pyridylacetate as an oil.

Workup

  1. customwas saturated at 0° C.
  2. extractionthe solution was extracted with 50 ml of diethyl ether
  3. washThe ethereal layer was washed successively with water
  4. dry with materiala suturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2d6bf61e39b146b58352126b68dd1358
Source dataset
uspto-grants-1989_10
Patent number
US04877795

Reaction notes

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