Acetic Acid → Dehydroparadol

HRID 2093244

反応式

HRID 2093244 の反応式
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]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 1183Vanillin2 回HCID 8082PiperidineHCID 131872-Nonanone

生成物 1

HCID 6438480Dehydroparadol収率 998.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-fa969dad883c4707ac9ec71cec865547
出典データセット
uspto-grants-2013_05
特許番号
US08445005B2

関連ノート

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