Eugenol → 4-Propylguaiacol

HRID 1635789

반응식

HRID 1635789 반응식
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1)[CH:2]=[CH2:3].C1(C)C=CC(S(NN)(=O)=O)=CC=1.CC([O-])=O.[Na+]>C(COC)OC.O>[CH3:12][O:11][C:6]1[CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[CH:9]=[CH:8][C:7]=1[OH:10]

참가 물질

6

반응물 3

HCID 3314EugenolHCID 15303P-ToluenesulfonylhydrazideHCID 517045Sodium Acetate

생성물 1

HCID 177394-Propylguaiacol수율 48.1%

시약·촉매·용매 2

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of 123 mg (0.75 mmole) of 4-allyl-2-methoxyphenol (eugenol) and 1.4 gm (7.5 mmole)of p-toluenesulfonhydrazide in 15 ml of dimethoxyethane under reflex was added a solution of 1.7 gm of NaOAc in 15 ml water over a 4 hour period. The mixture was cooled to room temperature, poured into 20 ml of water, and extracted three times with 30 ml of CH2Cl2. The combined organic layers were washed with 50 ml of water, dried over MgSO4, and concentrated under vacuo. The resulting solid was flash chromatographed over silica gel using 10% ethyl acetate in hexane to afford 60 mg of 2-methoxy-4-propylphenol in 48% yield.

후처리

  1. extractionextracted three times with 30 ml of CH2Cl2
  2. washThe combined organic layers were washed with 50 ml of water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuo
  5. customchromatographed over silica gel using 10% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-2f4fba126928419f8728e7e159f2c18d
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06511966B2

연결된 노트

불러오는 중…