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

HRID 1826446Notes

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-0ffb830baa06494dbf71fcf50b481245
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049444B2

Reaction notes

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