Hydrochloric Acid → HCID 13646084, compound

HRID 1588151Notes

Reaction equation

HRID 1588151 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:9]([O:10][CH2:11]OC)=[C:8]([O:14]C)[C:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[C:26]([O:27]C)=[C:25]([O:29][CH2:30]OC)[C:24]([CH2:33][CH2:34][OH:35])=[C:23]([O:36]C)[C:22]=2[O:38][CH2:39]OC)=[C:6]([O:42][CH2:43]OC)[C:5]=1[O:46]C.Cl.C(=O)([O-])O.[Na+].O=O>O1CCCC1.C(O)(C)C.CO.O1CCCC1.C(O)(C)C>[OH:1][CH2:2][CH2:3][C:4]1[C:5](=[O:46])[C:6]([O:42][CH3:43])=[C:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[C:26](=[O:27])[C:25]([O:29][CH3:30])=[C:24]([CH2:33][CH2:34][OH:35])[C:23](=[O:36])[C:22]=2[O:38][CH3:39])[C:8](=[O:14])[C:9]=1[O:10][CH3:11]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 516892Sodium BicarbonateHCID 13646076HCID 13646076, compound

Product 1

HCID 13646084HCID 13646084, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Conditions

Temperature
50 °C

Procedure

402 Milligrams of 4,4'-pentamethylenebis[1-(2-hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene] was dissolved in a mixed solvent of 4 ml of tetrahydrofuran with 4 ml of isopropanol, under ice-cooling conditions, 0.8 ml of tetrahydrofuran-isopropanol (1:1) solution containing 20% of hydrogen chloride was added thereto. The reaction mixture was heated at 50° C. on a water bath for 5 hours with stirring. The reaction mixture was concentrated, and to the residue obtained was added 10 ml of methanol and a small amount of sodium hydrogen carbonate, then whole mixture was heated at 50 to 60° C., on a water bath and oxygen gas was blown into the reaction mixture for 5 hours. After the reaction was completed, the reaction mixture was filtered, and concentrated, the residue obtained was treated by means of a preparative thin layer chromatography (silica gel plate: 20×20 cm, thickness 2 mm, 2 plates were used, developing solvent: ethyl acetate:benzene=1:1), then recrystallized from petroleum ether to obtain 305 mg of 5,5'-pentamethylenebis[2-(2-hydroxyethyl)-3,6-dimethoxy-1,4-benzoquinone] was obtained. Yellow needles crystals.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customto the residue obtained
  4. filtrationthe reaction mixture was filtered
  5. concentrationconcentrated
  6. customthe residue obtained
  7. additionwas treated by means of a preparative thin layer chromatography (silica gel plate
  8. customethyl acetate:benzene=1:1), then recrystallized from petroleum ether

Sources & evidence

ORD record
ord-d1b0970dc63649e5afb7036263220853
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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