Methyl iodide → 2',3,3',4,4',5-Hexamethoxybenzophenone
Reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)=[O:13].IC.[C:28]([O-])([O-])=O.[Na+].[Na+].COC1C=C(C(C2C=CC(OC)=C(OC)C=2OC)=O)C=C(OC)C=1>>[CH3:28][O:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=1)=[O:13]Participants
Procedure
(2-hydroxy-3,4-dimethoxyphenyl)-(3,4,5-trimethoxyphenyl)methanone (4.44 g, 12.75 mmol), iodomethane (1.59 ml, 25.51 mmol), and Na2CO3 (2.7 g, 25.51 mmol) were treated in the same manner as described above for the synthesis of (3,5-Dimethoxy-phenyl)-(2,3,4-trimethoxy-phenyl)-methanone. The crude material was purified via flash column chromatography (20% EtOAc in hexane) to give (2,3,4-trimethoxy-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone as an off-white solid (3.88 g, 84%); mp, 122-124° C.: 1HNMR (CDCl3) δ 7.11 (d, J=8 Hz, 1H, Ar), 7.08 (s, 2H, Ar), 6.73 (d, J=8 Hz, 1H, Ar), 3.94 (s, 6H, 2OCH3), 3.91 (s, 3H, OCH3), 3.86 (s, 6H, 2OCH3), 3.81 (s, 3H, OCH3); 13C NMR (DMSO-d6) δ 194.4, 156.1, 152.9, 152.7, 142.6, 142.3, 133.5, 126.5, 124.9, 107.6, 106.8, 62.1, 61.1, 56.4, 56.3; Anal. Calcd. For C19H22O7: C, 62.98; H, 6.12. Found: C, 63.14; H, 6.13. The product was carried over to the next step.
Workup
- customThe crude material was purified via flash column chromatography (20% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-f89e858200a74ff8a65fb9daa332b951
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312241B2
Reaction notes
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