(S,S)-2,4-dibenzylglutaric acid → (S,S)-2,4-dibenzylglutaric anhydride

HRID 374311Notes

Reaction equation

HRID 374311 reaction equation
[CH2:1]([C@H:8]([CH2:12][C@@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14](O)=[O:15])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(=O)C>[CH2:1]([C@@H:8]1[CH2:12][C@@H:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14](=[O:15])[O:10][C:9]1=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 14557654(S,S)-2,4-dibenzylglutaric acid

Product 1

HCID 14557658(S,S)-2,4-dibenzylglutaric anhydride

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

The (S,S)-2,4-dibenzylglutaric anhydride [mp 172°-174°; [alpha]D =-19.1° (c=1 in CHCl3)] is prepared similarly by refluxing (S,S)-2,4-dibenzylglutaric acid in acetyl chloride for 3 hours, concentrating the mixture and recrystallizing from toluene.

Workup

  1. concentrationconcentrating the mixture
  2. customrecrystallizing from toluene

Sources & evidence

ORD record
ord-babaef248cd1422a962570a49bf07328
Source dataset
uspto-grants-1992_11
Patent number
US05166212

Reaction notes

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