Bromoacetic Acid → HCID 85714256, compound

Participants

Reaction Conditions

Reaction Steps

Bromoacetic acid (16.01 grams, 0.1 mole) is dissolved in tetra-hydrofuran (200 ml.) and 1,1-carbonyldiimidazole (16.22 grams, 0.1 mole) is added and the mixture stirred for an hour at 25° C. tert.-Butyl 2-hydroxy-2-methylpropanoate (10.41 grams, 0.1 mole) is added and the mixture stirred for 18 hours at 25° C. The solvent is removed by evaporation in vacuo to give tert. butyl 2-(2-bromoacetoxy)-2-methylpropanoate acid (0.1 mole). This compound is dissolved in ether, dried over anhydrous magnesium sulfate, filtered and the solvent removed by evaporation in vacuo. The product is dissolved in 1-propanol (100 ml.) and bis-(2-hydroxyethyl)amine (10.51 grams, 0.1 mole) and triethylamine (11.1 grams, 0.1 mole) are added and the mixture is stirred and heated at reflux for 3 hours. The volatile material is evaporated in vacuo, the residue dissolved in ether (250 ml.), washed with water and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation in vacuo and dissolved in toluene (300 ml.). Methanesulfonic acid (2 grams) is added and the mixture refluxed for 2 hours. The mixture is cooled, extracted with water and the organic layer dried over anhydrous magnesium sulfate. The solvent is removed by evaporation in vacuo. The yield of 2-[N,N-bis-(2-hydroxyethyl)aminoacetoxy]-2-methylpropanoic acid is 17.45 g. (70%).

Provenance & Evidence