Trifluoroacetic acid → 5,6,7,8-Tetrahydro-1,2,3,10,11-pentamethoxydibenzo[a,c]cyclooctene

HRID 1109663Notes

Reaction equation

HRID 1109663 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:26][O:25][C:17]1[C:16]2[C:6]3[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=2[CH:20]=[C:19]([O:21][CH3:22])[C:18]=1[O:23][CH3:24]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 151355331-(3,4-Dimethoxyphenyl)-4-(3,4,5-trimethoxyphenyl)butane

Product 1

HCID 190209825,6,7,8-Tetrahydro-1,2,3,10,11-pentamethoxydibenzo[a,c]cycloocteneYield 24.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 1 ml of dichloromethane, 70 mg (0.194 mmol) of 1-(3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-butane were dissolved. The solution was added with 0.1 ml of trifluoroacetic acid and 180 mg (0.39 mmol) of ferric perchlorate, followed by stirring at room temperature for 40 minutes. The reaction mixture was dissolved in 20 ml of ethyl acetate. The resulting solution was washed with 2N-HCl and then with saturated NaCl. The organic layer was dried over anhydrous magnesium sulfate and the solvent was thereafter distilled off under reduced pressure, whereby brown oil was obtained. The oil thus obtained was purified by thin-film chromatography (silica gel: "MERCK #5744", eluent: 1:5 mixed solvent of ethyl acetate and hexane), whereby 17 mg of the title compound were obtained as colorless oil (yield: 24%). In addition, the starting material was recovered as colorless oil (15 mg, recovery: 21%).

Workup

  1. washThe resulting solution was washed with 2N-HCl
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was thereafter distilled off under reduced pressure, whereby brown oil
  4. customwas obtained
  5. customThe oil thus obtained
  6. customwas purified by thin-film chromatography (silica gel: "MERCK #5744", eluent: 1:5 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-8549f99e341e4500ab458b4c495c12d0
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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