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

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 natrium 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.

1. additionwas then added
2. waitthe mixture kept for additional 5 min. at 0° and for 2 h at ambient temperature
3. additionPouring
4. extractionice/HCl dil., twofold extraction with AcOEt
5. washwashing with brine
6. dry with materialdrying over natrium sulfate and evaporation of the solvents

ORD record

ord-8e53511544cd42e3a3d05a2fbba82823

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06642389B2