Iodine → HCID 15744528, compound

HRID 1647313Notes

Reaction equation

HRID 1647313 reaction equation
C1(C=CC2C=CC=CC=2)C=CC=CC=1.II.[C:17](C1C=CC=CC=1)(=[O:19])C.[CH3:26][O:27][C:28]1[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[C:39]2[C:38]3[C:33](=[CH:34][C:35](OC)=[CH:36][CH:37]=3)[CH:32]=[CH:31][C:30]=2[CH:29]=1>C1CCCCC1>[CH3:26][O:27][C:28]1[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[C:39]2[C:38]3[C:33](=[C:34]([O:19][CH3:17])[CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][C:30]=2[CH:29]=1

Participants

6

Reactant 4

HCID 807IodineHCID 7410AcetophenoneHCID 11502StilbeneHCID 114379782,3,4,7-tetramethoxyphenanthrene

Product 1

HCID 15744528HCID 15744528, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

The stilbene mixture containing 30c and 31c (1010 mg, 3.36 mmol) in cyclohexane (500 mL) containing iodine (53 mg) and acetophenone (1.71 mmol, 0.5 eq) was irradiated as in the above synthesis of 32a and 32c to give 32d (760 mg, 76%): mp 80°-82° C.; IR (KBr) 846 (2H adjacent), 790 cm-1 (3H adjacent); 1H NMR (CDCl3, 200 Mhz) δ9.12 (d, 1H, J=10 Hz), 8.20 (d, 1H, J=10 Hz), 7.57 (m, 2H), 7.10 (s, 1H), 6.99 (d, 1H, J=8 Hz), 4.03 (s, 6H), 4.02 (s, 3H), 4.00 (s, 3H); EIMS m/e 298 (M+, 100), 283 (40). Anal. (C18H18O4) C, H.

Sources & evidence

ORD record
ord-ddcbff33206742f9be96d9a35d82c970
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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