Perylene → 7-(3-Perylenoyl)heptanoic acid methyl ester
Reaction equation
COC(=O)C([C:10]([C:12]1[C:29]2=[C:30]3[C:19](C4C5C(=[CH:25][CH:26]=[CH:27][C:28]2=5)C=CC=4)=[CH:18][CH:17]=[CH:16][C:15]3=[CH:14][CH:13]=1)=[O:11])CCCCC.[CH3:33][O:34][C:35](=[O:60])[CH:36]([C:38]([C:40]1C2=C3C(C4C5C(=CC=CC2=5)C=CC=4)=CC=C[C:43]3=[CH:42][CH:41]=1)=O)C.[Cl-].COC(=O)CCC[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][C:73](O)=O.C1C2=C3C(C4C5C(=CC=CC2=5)C=CC=4)=CC=CC3=CC=1>>[CH3:33][O:34][C:35](=[O:60])[CH2:36][CH2:38][CH2:40][CH2:41][CH2:42][CH2:43][C:10]([C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:68]4[C:69]=3[C:70]([C:25]3[C:30]=2[C:29]=1[CH:28]=[CH:27][CH:26]=3)=[CH:71][CH:72]=[CH:73]4)=[O:11]Participants
5
Procedure
The synthesis and purification of perylenoylheptanoic acid methyl ester was achieved as described for perylenoyl propanoic acid methyl ester starting from sebacic acid monomethyl ester chloride and perylene. Yield 73.7%. Rf 0.23 (system 1). 1H-NMR (CDCl3) (δ, ppm): 1.43 (m, 4H, 4-CH2, 5-CH2), 1.67 (m, 2H, 3-CH2), 1.82 (m, 2H, 6-CH2), 2.32 (t, 2H, Ja,b=J2,3 7.42 Hz, 2-CH2), 3.05 (t, 2H, Ja,b=J6,7 7.35 Hz, 7-CH2), 3.69 (s, 3H, CH3), 7.43-7.64 (m, 3H, Ar), 7.74 (t, 2H, J 8.26 Hz, Ar), 7.84 (d, 1H, J 7.92 Hz, Ar), 8.13-8.30 (m, 4H, Ar), 8.48 (d, 1H, J 7.54 Hz, Ar).
Sources & evidence
- ORD record
- ord-7d634d8bd4414f93b30c51bb61cd4468
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601845B2
Reaction notes
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