Resorcinol → 4-(4-(Decyloxy)benzoyloxy)benzoic acid
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1.C1(C=CC=C(O)C=1)O.C(O[C:41]1[CH:57]=[CH:56][C:44]([C:45]([O:47]C2C=CC(C=O)=CC=2)=[O:46])=[CH:43][CH:42]=1)CCCCCCCCC.[O-]Cl=O.[Na+]>>[CH2:11]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:19][C:41]2[CH:57]=[CH:56][C:44]([C:45]([OH:47])=[O:46])=[CH:43][CH:42]=2)=[O:18])=[CH:15][CH:14]=1)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH3:2]Participants
5
Procedure
Synthesized as described above for compound 7. Quantities: resorcinol (3.18 g, 28.9 mmol), 10 (8.5 g, 22 mmol), NaH2PO4·H2O (10.39 g, 66.6 mmol), NaClO2 (11.65 g, 0.13 mol). Yield 8.8 g (quant.). 1H NMR: δH (CDCl3; 300 MHz): 0.91 (3 H, t, 3J=6.8 Hz, CH3), 1.23-1.59 (14 H, m, CH2), 1.85 (2 H, m, O—CH2—CH2), 4.07 (2 H, t, 3J=6.5 Hz, O—-CH2), 7.00 (2 H, d, 3J=8.9 Hz, Ar—H), 7.36 (2 H, d, 3J=8.6 Hz, Ar—H), 8.17 (2 H, d, 3J=8.9 Hz, Ar—H), 8.22 (2 H, d, 3J=8.6 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 14.5, 23.1, 26.4, 29.5, 29.7, 29.8, 30.0, 32.3, 68.8, 114.8, 121.4, 122.4, 127.0, 132.3, 132.8, 156.0, 164.2, 164.7, 171.7.
Workup
- customSynthesized
Sources & evidence
- ORD record
- ord-cfd716aac6e94d96a3a8bf29e6f7da19
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08092712B2
Reaction notes
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