Dichloromethane → HCID 19020980, compound

HRID 1109662Notes

Reaction equation

HRID 1109662 reaction equation
ClCCl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)[CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13].FC(F)(F)C(O)=O>C(OCC)(=O)C>[CH3:31][O:30][C:22]1[C:21]2[C:7]3[C:6]([O:5][CH3:4])=[C:11]([O:12][CH3:13])[C:10]([O:14][CH3:15])=[CH:9][C:8]=3[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=2[CH:25]=[C:24]([O:26][CH3:27])[C:23]=1[O:28][CH3:29]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 19020971HCID 19020971, compound

Product 1

HCID 19020980HCID 19020980, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dissolved in 1.2 ml (0.128 mmol) of dichloromethane were 50 mg (0.128 mmol) of 1,4-bis(3,4,5-trimethoxyphenyl)butane, followed by the addition of 0.12 ml of trifluoroacetic acid and 178 mg (0.39 mmol) of ferric perchlorate. After stirred 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 thereafter dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, whereby brown oil was obtained. The oil thus obtained was purified by TLC (silica gel: "MERCK #5744", eluent: 1:1 mixed solvent of ethyl acetate and hexane), whereby 3 mg of the title compound were obtained as colorless oil (yield: 6%).

Workup

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

Sources & evidence

ORD record
ord-32ddedba829a42dca39b63c98f6866d7
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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