1-(Phenylmethyl) butanedioate → Beta-carbobenzyloxypropionic acid anhydride
Reaction equation
[C:1]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]>C(OC(=O)C)(=O)C>[C:1]([CH2:11][CH2:12][C:13]([O:15][C:13](=[O:14])[CH2:12][CH2:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To 179 grams of beta-carbobenzyloxypropionic acid (IV) there are added 500 ml of acetic anhydride and the solution is heated on a boiling water bath for 45 minutes. The excess reactant is distilled off and the residue is crystallized from one liter of carbon tetrachloride, the result being 140 grams (81% of theory) of (VI), which has a melting point of 70°C-71°C.
Workup
- temperaturethe solution is heated on a boiling water bath for 45 minutes
- distillationThe excess reactant is distilled off