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Perylene → 7-(3-Perylenoyl)heptanoic acid methyl ester

HRID 501894
Notes
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Reaction equation

HRID 501894 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]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 9142PeryleneHCID 86605551Perylenoylheptanoic acid methyl esterHCID 86605552Perylenoyl propanoic acid methyl esterHCID 86605553Sebacic acid monomethyl ester chloride

Product 1

HCID 866055507-(3-Perylenoyl)heptanoic acid methyl esterYield 73.7%

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-1f5d0b644e494508a166f1b9941fe5da
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772402B2

Reaction notes

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