Hydrochloric Acid → HCID 19757184, compound

HRID 1588159Notes

Reaction equation

HRID 1588159 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][CH2:22][CH2:23][S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[C:35]([O:36][CH2:37]OC)=[C:34]([O:40]C)[CH:33]=[C:32]([O:42][CH2:43]OC)[C:31]=1[O:46]C.O1CCCC1.C(O)(C)C.Cl.C(OCC)(=O)C.CCCCCC>O1CCCC1.C(O)(C)C.CO>[CH3:37][O:36][C:35]1[C:34](=[O:40])[CH:33]=[C:32]([O:42][CH3:43])[C:31](=[O:46])[C:30]=1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][S:24][CH2:23][CH2:22][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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 19757180HCID 19757180, compoundHCID 21226206Ethyl acetate hexaneHCID 22597222Tetrahydrofuran 2-propanol

Product 1

HCID 19757184HCID 19757184, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

118.0 Milligrams (0.17 mmole) of bis{5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]pentyl} sulfide was dissolved in a mixed solvent of 1 ml of tetrahydrofuran--1 ml of isopropanol. The gas phase in the reaction vessel was replaced three times with argon gas under reduced pressure deaeration. 0.2 Milliliters of tetrahydrofuran-isopropanol solution containing 20% (by weight) of hydrogen chloride was added to the reaction vessel, and the reaction mixture was stirred at room temperature for 1 hour, then the temperature was elevated to 70° C., and the reaction was completed in an hour. The solvent was removed by evaporation under reduced pressure, then 2 ml of benzene was added to the residue, this mixture was further treated under reduced pressure to obtain light brawn oily product. This product was dissolved in 5 ml of methanol without purified, then this solution was heated to 40° C., a small amount of sodium hydrogen carbonate was added thereto, and oxygen gas was bubbled therein, and the reaction was completed in about 1 hour. The solvent was removed under reduced pressure, and the residue obtained was treated by means of a silica gel preparative thin layer chromatography (thickness: 1 mm, developing solvent: 50% ethyl acetate-n-hexane) to obtain 60.5 mg of bis[5-(3,6-dimethoxy-1,4-benzoquinon-2-yl)pentyl] sulfide. Yellow oily substance.

Workup

  1. additionwas added to the reaction vessel
  2. customwas elevated to 70° C.
  3. waitthe reaction was completed in an hour
  4. customThe solvent was removed by evaporation under reduced pressure
  5. addition2 ml of benzene was added to the residue
  6. additionthis mixture was further treated under reduced pressure
  7. customto obtain light brawn oily product
  8. customwithout purified
  9. temperaturethis solution was heated to 40° C.
  10. additiona small amount of sodium hydrogen carbonate was added
  11. customoxygen gas was bubbled
  12. waitthe reaction was completed in about 1 hour
  13. customThe solvent was removed under reduced pressure
  14. customthe residue obtained

Sources & evidence

ORD record
ord-13b55884838643da88899933a18acf33
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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