Acetic Acid → 1-(3-Hydroxy-4-methoxyphenyl)-7-phenylhept-1-en-3-one

HRID 1032858Notes

Reaction equation

HRID 1032858 reaction equation
N1CCCC1.C(O)(=O)C.[C:10]1([CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:22])[CH3:21])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O=[CH:24][C:25]1[CH:33]=[CH:32][C:29]([O:30][CH3:31])=[C:27]([OH:28])[CH:26]=1.Cl>C(OCC)C.C(OCC)(=O)C>[OH:28][C:27]1[CH:26]=[C:25]([CH:24]=[CH:21][C:20](=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:33]=[CH:32][C:29]=1[O:30][CH3:31]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 12127IsovanillinHCID 265306-Phenylhexan-2-oneHCID 31268Pyrrolidine

Product 1

HCID 543785401-(3-Hydroxy-4-methoxyphenyl)-7-phenylhept-1-en-3-oneYield 28%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyrrolidine (2.42 g, 34.0 mMol) is added to acetic acid (2.04 g, 34.0 mMol), and the mixture is stirred at room temperature for 20 minutes. After this time, 6-phenyl-2-hexanone (4.00 g, 22.6 mMol) as a solution in diethyl ether (20 ml) is added, and the mixture is allowed to stir for an additional 15 minutes. An ethereal solution of iso-vanillin (3.45 g, 22.5 mMol) is then added dropwise. The reaction mixture is stirred for 48 hours. HCl (1.0N, 30 ml) is then added to the reaction mixture, and the contents stirred for 20 minutes. The mixture is then taken up into an equal volume of ethyl acetate, and the phases separated. The organic layer is washed with saturated aqueous sodium bicarbonate, dried (sodium sulfate), and concentrated. The residue is chromatographed (silica gel; hexane/ethyl acetate 3:1) to afford 1.0 g (28%) of 1-(3-hydroxy-4-methoxyphenyl)-7-phenyl-1-hepten-3-one, mp=70°-75° C. C, H analysis: Calcd. for C20H22O3 (77.39, 7.14); Found (77.68, 6.94). The procedure of Example 1 is within that described in the above cited reference by Itokawa H. et al in the Chem. Pharm. Bull. Similarly prepared are Examples 2-12 using the procedure of Example 1.

Workup

  1. stirringto stir for an additional 15 minutes
  2. stirringThe reaction mixture is stirred for 48 hours
  3. stirringthe contents stirred for 20 minutes
  4. customthe phases separated
  5. washThe organic layer is washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residue is chromatographed (silica gel; hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-e4097e9a470e4a23a319178251a3a220
Source dataset
uspto-grants-1990_09
Patent number
US04959503

Reaction notes

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