1-(Phenylmethyl) butanedioate → Beta-carbobenzyloxypropionic acid anhydride

HRID 1287337Notes

Reaction equation

HRID 1287337 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

HCID 87881-(Phenylmethyl) butanedioate

Product 1

HCID 12428999Beta-carbobenzyloxypropionic acid anhydride

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

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

  1. temperaturethe solution is heated on a boiling water bath for 45 minutes
  2. distillationThe excess reactant is distilled off
  3. customthe residue is crystallized from one liter of carbon tetrachloride

Sources & evidence

ORD record
ord-2f6223bca9034c5f8a2b2f41d8bd4370
Source dataset
uspto-grants-1976_10
Patent number
US03984461

Reaction notes

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