Hydrochloric Acid → HCID 19757233, compound

HRID 1588158Notes

Reaction equation

HRID 1588158 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9]COC)=[CH:7][C:6]([O:13][CH3:14])=[C:5]([O:15]COC)[C:4]=1[CH2:19][CH2:20][CH2:21][S:22][S:23][CH2:24][CH2:25][CH2:26][C:27]1[C:32]([O:33][CH2:34]OC)=[C:31]([O:37]C)[CH:30]=[C:29]([O:39][CH2:40]OC)[C:28]=1[O:43]C.Cl.C(OCC)(=O)C.C1C=CC=CC=1>O1CCCC1.C(O)(C)C.CO>[CH3:34][O:33][C:32]1[C:31](=[O:37])[CH:30]=[C:29]([O:39][CH3:40])[C:28](=[O:43])[C:27]=1[CH2:26][CH2:25][CH2:24][S:23][S:22][CH2:21][CH2:20][CH2:19][C:4]1[C:5](=[O:15])[C:6]([O:13][CH3:14])=[CH:7][C:8](=[O:9])[C:3]=1[O:2][CH3:1]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 19757188HCID 19757188, compoundHCID 21583983Benzene ethyl acetate

Product 1

HCID 19757233HCID 19757233, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

259.7 Milligrams of bis{3-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propyl} disulfide was dissolved in a mixed solvent of 4 ml of tetrahydrofuran with 4 ml of isopropanol. The gas phase in the reaction vessel was replaced with argon gas three times under reduced pressure deaeration. 1 Milliliter of tetrahydrofuranisopropanol solution containing 20% (by weight) of hydrogen chloride was added to the reaction mixture, and the reaction mixture was heated at 70° C. with stirring, the reaction was completed in about 1 hour. The solvent was removed by evaporation under reduced pressure, then 5 ml of benzene was added to the residue, this mixture was further treated under reduced pressure to obtain light brawn oily substance. The crude substance was dissolved in 10 ml of methanol without being purified, and to this solution a small amount of sodium hydrogen carbonate was added, and oxygen gas was bubbled thereinto at room temperature for about 2 hours. The solvent was removed by evaporation under reduced pressure, the residue obtained was treated by means of a silica gel preparative thin layer chromatography (thickness: 1 mm, developing solvent: 50% ethyl acetate-benzene) to obtain 45.0 mg of bis[3-(3,6-dimethoxy-1,4-benzoquinon-2-yl)propyl]disulfide. Yellow oily substance.

Workup

  1. additionwas added to the reaction mixture
  2. customThe solvent was removed by evaporation under reduced pressure
  3. addition5 ml of benzene was added to the residue
  4. additionthis mixture was further treated under reduced pressure
  5. customto obtain light brawn oily substance
  6. customwithout being purified
  7. additionto this solution a small amount of sodium hydrogen carbonate was added
  8. customoxygen gas was bubbled
  9. waitat room temperature for about 2 hours
  10. customThe solvent was removed by evaporation under reduced pressure
  11. customthe residue obtained

Sources & evidence

ORD record
ord-41fe862f099c47019f40f3047ef44bf6
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

Loading…