Sodium Acetate → 1-Hexylpyrrole-2,5-dione

HRID 428936Notes

Reaction equation

[CH2:1]([NH:7][C:8](=[O:14])[CH:9]=[CH:10][C:11]([OH:13])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[CH2:1]([N:7]1[C:8](=[O:14])[CH:9]=[CH:10][C:11]1=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 110 °C

Procedure

4-(Hexylamino)-4-oxo-2-butenoic acid (Preparation 54, 75.8 g, 0.38 mol) was partially dissolved in acetic anhydride (1.5 l) and sodium acetate (125.6 g, 0.19 mol) was added in one portion. The reaction mixture was gradually heated to 110° C. for 4 h. Acetic anhydride was removed in vacuo and the title compound was obtained by vacuum distillation of the crude residue to give a colourless oil (49.8 g, 72%) which partially crystallised upon standing.

Workup

customAcetic anhydride was removed in vacuo

Sources & evidence

ORD record: ord-83d2d8f8b8aa4d9882b86b8a9841c208
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313312B1

Reaction notes

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