Hydrochloric Acid → 5-[(E)-2-(3,5-Dimethoxyphenyl)ethenyl]-2-methoxyphenol

HRID 2199493ノート

反応式

HRID 2199493 の反応式
[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]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 13888665Phenol, 5-[2-(3,5-dimethoxyphenyl)ethenyl]-2-methoxy-, acetate, (E)-

生成物 1

HCID 53850865-[(E)-2-(3,5-Dimethoxyphenyl)ethenyl]-2-methoxyphenol収率 86.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  1. temperaturereflux
  2. customafter completion of the reaction
  3. extractionextract three times with ethyl acetate, pool the organic layer
  4. dry with materialdry the solution over anhydrous magnesium sulfate
  5. filtrationFilter
  6. customevaporate the solvent in the solution
  7. dissolutionredissolve the residue with petroleum ether/ethyl acetate
  8. customrecrystallize

出典と根拠

ORDレコード
ord-a06bcce6a68047aeb0a92d78948acda9
出典データセット
uspto-grants-2016_06
特許番号
US09359298B2

反応ノート

読み込み中…