Resorcinol → 4-({4-[(Undec-10-en-1-yl)oxy]benzoyl}oxy)benzoic acid
Reaction equation
BrCCCCCCCCCC[O:12]C1C=CC(C(O)=O)=CC=1.C1(C=CC=C(O)C=1)O.[CH2:30]([O:41][C:42]1[CH:58]=[CH:57][C:45]([C:46]([O:48][C:49]2[CH:54]=[CH:53][C:52]([CH:55]=[O:56])=[CH:51][CH:50]=2)=[O:47])=[CH:44][CH:43]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40].[O-]Cl=O.[Na+]>>[CH2:30]([O:41][C:42]1[CH:58]=[CH:57][C:45]([C:46]([O:48][C:49]2[CH:54]=[CH:53][C:52]([C:55]([OH:12])=[O:56])=[CH:51][CH:50]=2)=[O:47])=[CH:44][CH:43]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40]Participants
5
Procedure
Synthesized as described above for compound 7. Quantities: resorcinol (1.71 g, 16 mmol), 13 (5.07 g, 13 mmol), NaH2PO4·H2O (5.32 g, 39 mmol), NaClO2 (6.71 g, 74 mmol). Yield 5.34 g (quant.). 1H NMR: δH (CDCl3; 300 MHz): 1.24-1.52 (12 H, m, CH2), 1.83 (2 H, m, O—CH2—CH2), 2.04 (2 H, m, CH2═CH—CH2), 4.05 (2 H, t, 3J=6.5 Hz, O—CH2), 4.95 (2 H, m, CH2═CH), 5.82 (1 H, m, CH2═CH), 6.99 (2 H, d, 3J=8.9 Hz, Ar—H), 7.34 (2 H, d, 3J=8.6 Hz, Ar—H), 8.16 (2 H, d, 3J=8.9 Hz, Ar—H), 8.20 (2 H, d, 3J=8.6 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 26.0, 28.9, 29.1, 29.3, 29.4, 29.5, 33.8, 68.4, 114.1, 114.4, 121.0, 122.0, 126.5, 131.9, 132.4, 139.2, 155.5, 163.8, 170.6.
Workup
- customSynthesized
Sources & evidence
- ORD record
- ord-b5aecd0290e14a51b4e08885c3e3cd49
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08092712B2
Reaction notes
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