Bromoacetic Acid → 2-(but-3-en-1-yloxy)acetic acid

HRID 2215196Notes

Reaction equation

HRID 2215196 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH:5]=[CH2:6].Br[CH2:9][C:10]([OH:12])=[O:11]>C1COCC1>[CH2:3]([O:7][CH2:9][C:10]([OH:12])=[O:11])[CH2:4][CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 693893-Buten-1-ol

Product 1

HCID 135414932-(but-3-en-1-yloxy)acetic acidYield 126.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 480 mg of NaH (50% in mineral oil, ˜20 mmol) in 10 ml of abs. THF was added at 0° 721 mg of 3-buten-1-ol (10 mmol) and the mixture stirred for 5 Min. (H2-evolution). 1.39 g of bromo-acetic acid (10 mmol), dissolved in 10 ml of THF, was then added and the mixture kept for additional 5 Min. at 0° and for 2 h at ambient temperature. Pouring onto crashed ice/HCl dil., twofold extraction with AcOEt, washing with brine, drying over sodium sulfate and evaporation of the solvents afforded 1.65 g of the title compound, contaminated with mineral oil, but sufficiently pure for the next step.

Workup

  1. additionwas then added
  2. additionPouring
  3. extractionice/HCl dil., twofold extraction with AcOEt
  4. washwashing with brine
  5. dry with materialdrying over sodium sulfate and evaporation of the solvents

Sources & evidence

ORD record
ord-ace497315ed64f849481be2ef0682849
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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