Perylenebutanoic acid → 8-(3-Perylenyl)octanoic acid

HRID 1819820Notes

Reaction equation

C1(CCCC(O)=O)C2=C3C(C4C5C(=CC=CC2=5)C=CC=4)=CC=CC3=CC=1.C[O:28][C:29](=[O:58])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([C:38]1[CH:39]=[CH:40][C:41]2[C:42]3[CH:43]=[CH:44][CH:45]=[C:46]4[C:57]=3[C:50]([C:51]3[C:56]=2[C:55]=1[CH:54]=[CH:53][CH:52]=3)=[CH:49][CH:48]=[CH:47]4)=O>>[CH:40]1[C:41]2=[C:56]3[C:51]([C:50]4[C:57]5[C:46](=[CH:45][CH:44]=[CH:43][C:42]2=5)[CH:47]=[CH:48][CH:49]=4)=[CH:52][CH:53]=[CH:54][C:55]3=[C:38]([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][C:29]([OH:58])=[O:28])[CH:39]=1

Participants

Reactant 2

HCID 86605548Perylenebutanoic acid

HCID 866055507-(3-Perylenoyl)heptanoic acid methyl ester

Product 1

HCID 859690388-(3-Perylenyl)octanoic acid

Procedure

The synthesis and isolation was accomplished under identical conditions as described for perylenebutanoic acid starting from 7-(3-perylenoyl)heptanoic acid methyl ester yielding 60.0% perylenyloctanoic acid. Rf 0.63 (system 3). 1H-NMR (CDCl3/CD3OD, 9:1) (δ, ppm): 1.25-1.50 (m, 6H, 3(CH2)), 1.59 (m, 2H, 3-CH2), 1.72 (m, 2H, 7-CH2), 2.26 (dt, 2H, Ja,b 1.79 Hz, J2,3 7.45 Hz, 2-CH2), 2.97 (t, 2H, J7,8 7.72 Hz, 8-CH2), 7.28 (d, 1H, J 8.0 Hz, Ar), 7.43 (m, 3H, Ar), 7.59 (d, 1H, J 3.42 Hz, Ar), 7.63 (d, 1H, J 3.42 Hz, Ar), 7.83 (d, 1H, J 8.54 Hz, Ar), 8.10-8.22 (m, 4H, Ar).

Workup

customThe synthesis and isolation

Sources & evidence

ORD record: ord-912f4fcf186e4e7396ddd658166c725d
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601845B2

Reaction notes

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