Succinic anhydride → HCID 54489600, compound

HRID 1109712Notes

Reaction equation

HRID 1109712 reaction equation
[CH:1]1[C:18]2[C:19]3[C:24]4[C:3](=[CH:4][CH:5]=[C:6]5[C:23]=4[C:22]4[C:9](=[CH:10][CH:11]=[C:12]6[C:21]=4[C:20]=3[C:15](=[CH:16][CH:17]=2)[CH:14]=[CH:13]6)[CH:8]=[CH:7]5)[CH:2]=1.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O.C1(C)C(C)=CC=CC=1.C1COCC1>[C:2]1([C:25]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:31])[C:3]2[C:24]3[C:19]4[C:18](=[CH:17][CH:16]=[C:15]5[C:20]=4[C:21]4[C:12](=[CH:11][CH:10]=[C:9]6[C:22]=4[C:23]=3[C:6](=[CH:5][CH:4]=2)[CH:7]=[CH:8]6)[CH:13]=[CH:14]5)[CH:1]=1

Participants

7

Reactant 3

HCID 7922Succinic anhydrideHCID 9115Coronene3×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 54489600HCID 54489600, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 7237O-XyleneSolventHCID 7416NitrobenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A Friedel-Crafts acylation of coronene was performed using the procedure of Clar and Zanders J. Chem. Soc. 2, (1958) 1577-1579, with the Coronene (100mg; FIG. 1, compound I) and succinic anhydride (73.4mg) were placed in a 10ml round-bottomed flask. Aluminum chloride (400mg) was dissolved in 3ml of nitrobenzene and injected slowly into the round-bottomed flask. The flask was then flushed with nitrogen and sealed. The mixture was stirred for four hours and cold 2M HCl (8ml) was added and the solution boiled for 10 minutes. A greenish-yellow precipitate was obtained. The crystals were filtered, washed with benzene, methanol and 2M HCl, and dried overnight under vacuum. The product (108mg; 82% yield) was recrystallized from xylene and judged pure using TLC analyses (Rf=0.53), using 50% ethanol/50% THF (v/v) as the developing solvent with silica gel G (40 micron) as the support medium. The keto-acid (FIG. 1, compound II) had a melting point of 243° C. IR and NMR analysis gave spectra consistent with the structure of the molecule, and in xylene had an absorption band at 444 nm, with ε340 in THF=24,914±80M-1 cm-1.

Workup

  1. customThe flask was then flushed with nitrogen
  2. customsealed
  3. additioncold 2M HCl (8ml) was added
  4. waitthe solution boiled for 10 minutes
  5. customA greenish-yellow precipitate was obtained
  6. filtrationThe crystals were filtered
  7. washwashed with benzene, methanol and 2M HCl
  8. customdried overnight under vacuum
  9. customThe product (108mg; 82% yield) was recrystallized from xylene
  10. customIR and NMR analysis gave spectra consistent with the structure of the molecule

Sources & evidence

ORD record
ord-474d0ac5e2814512a35a4d2178154e79
Source dataset
uspto-grants-1994_06
Patent number
US05322794

Reaction notes

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