Hydrochloric Acid → 5-[(E)-2-(3,5-Dimethoxyphenyl)ethenyl]-2-methoxyphenol
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19]C(=O)C)[CH:12]=2)[CH:6]=[C:5]([O:23][CH3:24])[CH:4]=1.C[O-].[Na+].Cl>CO>[CH3:24][O:23][C:5]1[CH:6]=[C:7](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([OH:19])[CH:12]=2)[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1Participants
Procedure
Dissolve compound 21c (5.0 g, 0.015 mol) in anhydrous methanol (50 ml), add in sodium methoxide (1.41 g, 0.024 mol), reflux to react for 3h, after completion of the reaction, pour the reaction solution into ice water, adjust pH to less than 2 with dilute hydrochloric acid, extract three times with ethyl acetate, pool the organic layer, dry the solution over anhydrous magnesium sulfate. Filter, and evaporate the solvent in the solution, redissolve the residue with petroleum ether/ethyl acetate, recrystallize to obtained a white solid (3.70 g, 85%). 1H NMR (400 MHz, DMSO-d6): 3.75 (s, 3H), 3.81 (s, 6H), 6.24 (s, 1H), 6.86 (s, 2H), 6.93 (d, J=16.0 Hz, 1H), 7.01 (d, J=16.0 Hz, 1H), 7.08 (d, J=7.6 Hz, 1H), 7.13 (d, J=7.6 Hz, 1H), 7.15 (s, 1H), 9.89 (s, 1H).
Workup
- temperaturereflux
- customafter completion of the reaction
- extractionextract three times with ethyl acetate, pool the organic layer
- dry with materialdry the solution over anhydrous magnesium sulfate
- filtrationFilter
- customevaporate the solvent in the solution
- dissolutionredissolve the residue with petroleum ether/ethyl acetate
- customrecrystallize
Sources & evidence
- ORD record
- ord-a06bcce6a68047aeb0a92d78948acda9
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359298B2
Reaction notes
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