Hydrochloric Acid → HCID 13922668, compound

HRID 1588169Notes

Reaction equation

HRID 1588169 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9]COC)=[C:7]([Cl:13])[C:6]([O:14][CH3:15])=[C:5]([O:16]COC)[C:4]=1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[C:30]([O:31]COC)=[C:29]([O:35][CH3:36])[CH:28]=[C:27]([O:37]COC)[C:26]=1[O:41][CH3:42].Cl.C(OCC)(=O)C.CCCCCC>C(O)C.O1CCCC1.C(#N)C.C(OCC)(=O)C>[CH3:15][O:14][C:6]1[C:5](=[O:16])[C:4]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[C:30](=[O:31])[C:29]([O:35][CH3:36])=[CH:28][C:27](=[O:37])[C:26]=2[O:41][CH3:42])=[C:3]([O:2][CH3:1])[C:8](=[O:9])[C:7]=1[Cl:13]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 19757234HCID 19757234, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 13922668HCID 13922668, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolventHCID 21873804Tetrahydrofuran ethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

219 Milligrams (0.35 mM) of 1-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-chlorophenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]pentane was dissolved in 5 ml of a mixed solvent of ethanol-tetrahydrofuran (1:1), to this solution was added 0.5 ml of a mixed solvent of ethanol-tetrahydrofuran (1:1) containing 20% of hydrogen chloride under an atmosphere of argon gas at a room temperature, then the reaction mixture was stirred for 2 hours at 60° C. The solvent was removed under reduced pressure, to the residue was added 5 ml of benzene, and the mixture was again treated under reduced pressure to remove the hydrogen chloride. The residue obtained was dissolved in 20 ml of acetonitrile, further added 1.5 ml of acetonitrile solution of complex of Cu4Cl4O2 (CH3CN)3 (which was prepared by adding 1 g of cuprous chloride in 25 ml of acetonitrile under bubbling oxygen gas), and the reaction mixture was stirred for 1 hour under oxygen gas stream conditions. The solvent was removed under reduced pressure, the residue obtained was dissolved in 30 ml of ethyl acetate, then the organic layer was washed three times with 10 ml of water, then washed once with 10 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, then concentrated under a reduced pressure. The residue obtained was treated by means of a silica gel thin layer chromatography (adsorbent: Silica gel 60 F254, E. Merck A. G.-thickness: 1 mm, developing solvent: 50% ethyl acetate-n-hexane) to obtain 107 mg of 2,5-dimethoxy-3-chloro-6-[5-(2,5-dimethoxy-1,4-benzoquinon-3-yl)pentyl]-1,4-benzoquinone. Orange powdery substance.

Workup

  1. customThe solvent was removed under reduced pressure, to the residue
  2. additionwas added 5 ml of benzene
  3. additionthe mixture was again treated under reduced pressure
  4. customto remove the hydrogen chloride
  5. customThe residue obtained
  6. customThe solvent was removed under reduced pressure
  7. customthe residue obtained
  8. washthe organic layer was washed three times with 10 ml of water
  9. washwashed once with 10 ml of a saturated sodium chloride aqueous solution
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under a reduced pressure
  12. customThe residue obtained

Sources & evidence

ORD record
ord-814a8c7bf0714fd181424c345313dcd6
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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