Acetone → (E)-methyl 2-[2-(hydroxymethyl)phenyl]-3-methoxypropenoate

HRID 991414노트

반응식

HRID 991414 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].CC(C)=[O:19]>O.[N+]([O-])([O-])=O.[Ag+]>[OH:19][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11]

참가 물질

5

반응물 2

HCID 180AcetoneHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate

생성물 1

HCID 70155576(E)-methyl 2-[2-(hydroxymethyl)phenyl]-3-methoxypropenoate수율 54%

시약·촉매·용매 2

HCID 24470Silver Nitrate촉매HCID 962Water용매

반응 조건

온도
2 °C

실험 절차

(E)-Methyl 2-[2-(bromomethyl)phenyl]-3-methoxypropenoate (15 g) was dissolved in acetone (200 ml) and the solution was cooled to 2° C. A solution of silver nitrate (22.35 g) in water (200 ml) at 4° C. was added to this. The temperature rose to 12° C. After stirring for 40 minutes the green/grey precipitate which had formed was filtered off and the filtrate partitioned between water and diethyl ether. The diethyl ether layer was washed with brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure to give an oil which was purified by chromatography on silica gel, eluting with diethyl ether, to give (E)-methyl 2-[2-(hydroxymethyl)phenyl]-3-methoxypropenoate as a viscous oil (6.33 g, 54%). 1H NMR (CDCl3): 2.3(t,1H), 3.7(s,3H), 3.8(s,3H), 4.5(d,2H), 7.1(m,1H), 7.2-7.4(m,2H), 7.5(m,1H), 7.6(s,1H) ppm.

후처리

  1. customrose to 12° C
  2. customhad formed
  3. filtrationwas filtered off
  4. customthe filtrate partitioned between water and diethyl ether
  5. washThe diethyl ether layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated under reduced pressure
  8. customto give an oil which
  9. customwas purified by chromatography on silica gel
  10. washeluting with diethyl ether

출처 및 근거

ORD 기록
ord-d1ef65fc0be94d9882474dce9c94a253
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465457B1

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