Acetic Acid → Dehydroparadol

HRID 2093244

Reaction equation

HRID 2093244 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 6438480DehydroparadolYield 998.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-fa969dad883c4707ac9ec71cec865547
Source dataset
uspto-grants-2013_05
Patent number
US08445005B2

Linked notes

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