Resorcinol → 4-{[4-(Dodecyloxy)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:42][C:43]1[CH:59]=[CH:58][C:46]([C:47]([O:49][C:50]2[CH:55]=[CH:54][C:53]([CH:56]=[O:57])=[CH:52][CH:51]=2)=[O:48])=[CH:45][CH:44]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].[O-]Cl=O.[Na+]>>[CH2:30]([O:42][C:43]1[CH:44]=[CH:45][C:46]([C:47]([O:49][C:50]2[CH:55]=[CH:54][C:53]([C:56]([OH:12])=[O:57])=[CH:52][CH:51]=2)=[O:48])=[CH:58][CH:59]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]Participants
5
Procedure
Synthesized as described above for compound 7. Quantities: resorcinol (1.79 g, 16 mmol), 11 (5.52 g, 13 mmol), NaH2PO4·H2O (6.29 g, 40 mmol), NaClO2 (7.03 g, 77 mmol). Yield 5.55 g (quant.). 1H NMR: δH (CDCl3; 300 MHz): 0.89 (3 H, t, 3J=6.9 Hz, CH3), 1.17-1.71 (18 H, m, CH2), 1.83 (2 H, m, O—CH2—CH2), 4.05 (2 H, t, 3J=6.6 Hz, O—CH2), 6.99 (2 H, d, 3J=8.9 Hz, Ar—H), 7.35 (2 H, d, 3J=8.6 Hz, Ar—H), 8.14 (2 H, d, 3J=8.9 Hz, Ar—H), 8.17 (2 H, d, 3J=8.6 Hz, Ar—H). 13C NMR: δC (CDCl3; 300 MHz): 14.1, 22.7, 26.0, 29.1, 29.3, 29.5, 29.6, 29.6, 29.7, 31.9, 68.4, 114.4, 120.9, 122.0, 126.5, 131.9, 132.4, 155.5, 170.3.
Workup
- customSynthesized
Sources & evidence
- ORD record
- ord-c5f24b1787c042d7adf396f036729dfd
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08092712B2
Reaction notes
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