Hydrochloric Acid → 2-(PENTAN-3-YLOXY)ACETIC ACID

HRID 1064370Notes

Reaction equation

HRID 1064370 reaction equation
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[CH2:10][C:11]([O-:13])=[O:12].[Na+].Cl>O1CCCC1.O>[CH2:2]([CH:3]([O:6][CH2:10][C:11]([OH:13])=[O:12])[CH2:4][CH3:5])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 114283-PentanolHCID 24758Sodium hydrideHCID 23665759Sodium chloroacetate

Product 1

HCID 222732322-(PENTAN-3-YLOXY)ACETIC ACIDYield 31.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 198 mg of 3-pentanol in tetrahydrofuran (4 ml), 180 mg of sodium hydride was added in nitrogen atmosphere at 0° C., and stirred for an hour at room temperature. To the solution 261 mg of sodium chloroacetate was added, followed by 2 hours' stirring at 100° C. The reaction solution was cooled to room temperature, diluted with water, acidified with 1N hydrochloric acid and extracted with chloroform. The chloroform layer was dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to provide 103 mg of the title compound.

Workup

  1. stirring' stirring at 100° C
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform layer was dried on anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1aadd23a9c684b0c84f901c18803186d
Source dataset
uspto-grants-2005_11
Patent number
US06969712B2

Reaction notes

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