Acetic Acid → Dehydroparadol

HRID 2093244

반응식

HRID 2093244 반응식
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH3:12][C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(O)(=O)C.N1CCCCC1>CCCCCC.C(OCC)C>[OH:9][C:8]1[CH:10]=[CH:11][C:3](/[CH:2]=[CH:12]/[C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:4][C:5]=1[O:6][CH3:7]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 1183Vanillin2회HCID 8082PiperidineHCID 131872-Nonanone

생성물 1

HCID 6438480Dehydroparadol수율 998.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

실험 절차

10 g (6.5 mmol) of vanillin and 9.3 g (6.5 mmol) of 2-nonanone were dissolved by stirring in 30 ml of hexane and 20 ml of diethyl ether. Moreover, after adding 3.9 g of acetic acid, 4.6 ml (6.5 mmol) of piperidine was added followed by stirring for 6 hours. Following completion of the reaction, unreacted vanillin was removed with an aqueous sodium bicarbonate solution followed by extraction with diethyl ether. After drying with anhydrous magnesium sulfate, the solvent was distilled off to obtain 20.2 g of crude product. The crude product was purified by column chromatography (SiO2/CHCl3) to obtain (E)-1-(4′-hydroxy-3′-methoxyphenyl)dec-1-en-3-one (17.94 g, yield: 90%).

후처리

  1. additionwas added
  2. customwas removed with an aqueous sodium bicarbonate solution
  3. extractionfollowed by extraction with diethyl ether
  4. dry with materialAfter drying with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customto obtain 20.2 g of crude product
  7. customThe crude product was purified by column chromatography (SiO2/CHCl3)

출처 및 근거

ORD 기록
ord-fa969dad883c4707ac9ec71cec865547
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445005B2

연결된 노트

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