Hydrochloric Acid → (2-Methyl-but-3-enyloxy)-acetic acid

HRID 1432100Notes

Reaction equation

HRID 1432100 reaction equation
[CH3:1][CH:2]([CH:5]=[CH2:6])[CH2:3][OH:4].[H-].[Na+].[C:9]([O:12]I)(=[O:11])[CH3:10].[Na].Cl>C1COCC1.O.[Cl-].[Na+].O>[CH3:1][CH:2]([CH:5]=[CH2:6])[CH2:3][O:4][CH2:10][C:9]([OH:12])=[O:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 942922-Methyl-3-buten-1-olHCID 86611583HCID 86611583, compound

Product 1

HCID 10080518(2-Methyl-but-3-enyloxy)-acetic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Under nitrogen atmosphere a suspension of 0.5 g (5.81 mmol) 2-methyl-3-buten-1-ol and 0.348 g (8.71 mmol, 60% suspension in mineral oil) NaH in 10 ml THF are stirred 3 h at rt. Solid sodium iodo acetate (1.81 g, 8.71 mmol) is added and stirring is continued for 2 h. The mixture is diluted with water and brine, acidified with 1N HCl and extracted with EtOAc. The organic phase is dried with sodium sulfate and concentrated. the residue is kugelrohr distilled at ca 1 mbar (70-110° C.) to yield the title compound as a colorless liquid.

Workup

  1. stirringstirring
  2. waitis continued for 2 h
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase is dried with sodium sulfate
  5. concentrationconcentrated
  6. distillationthe residue is kugelrohr distilled at ca 1 mbar (70-110° C.)

Sources & evidence

ORD record
ord-35c6ff1aa2b94935a9f8a0cf1453e540
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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