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

HRID 2199493노트

반응식

HRID 2199493 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a06bcce6a68047aeb0a92d78948acda9
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359298B2

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