Hydrochloric Acid → HCID 19020974, compound

HRID 1109654Notes

Reaction equation

HRID 1109654 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]([C:32]([O:34][CH3:35])=[O:33])([C:28]([O:30][CH3:31])=[O:29])[CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].FC(F)(F)C(O)=O.Cl>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]2[C:17]3[C:18]([O:26][CH3:27])=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:16]=3[CH2:15][C:14]([C:32]([O:34][CH3:35])=[O:33])([C:28]([O:30][CH3:31])=[O:29])[CH2:13][C:5]=2[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 19020979HCID 19020979, compound

Product 1

HCID 19020974HCID 19020974, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolved in 4 ml of dichloromethane were 200 mg (0.41 mmol) of dimethyl 1,3-bis(3,4,5-trimethoxyphenyl)propane-2,2-dicarboxylate. The solution was added with 0.4 ml of trifluoroacetic acid and 580 mg (1.25 mmol) of ferric perchlorate, followed by stirring at room temperature for 2 hours. After the reaction mixture was added with 2N-HCl and then dissolved in 20 ml of ethyl acetate, the water layer was removed. The organic layer was washed with water and then with saturated NaHCO3, and then was dried over anhydrous magnesium sulfate. The solvent was thereafter distilled off under reduced pressure. The residue thus obtained was purified by column chromatography (silica gel: "MERCK #9385", 10 g, eluent: 1:1 mixed solvent of ethyl acetate and hexane), whereby 183 mg of the title compound were obtained as a colorless solid (yield: 92%).

Workup

  1. customthe water layer was removed
  2. washThe organic layer was washed with water
  3. dry with materialwith saturated NaHCO3, and then was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was thereafter distilled off under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by column chromatography (silica gel: "MERCK #9385", 10 g, eluent: 1:1 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-633f097232b542f1a51b0639eb51b33c
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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