Hydrochloric Acid → 1-(2,5-Dimethoxy-6-butyl-1,4-benzoquinone-3-yl)-5-[2,5-dimethoxy-6-(2-hydroxyethyl)-1,4-benzoquinon-3-yl]pentane

HRID 1588143Notes

Reaction equation

HRID 1588143 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9]COC)=[C:7]([CH2:13][CH2:14][CH2:15][CH3:16])[C:6]([O:17][CH3:18])=[C:5]([O:19]COC)[C:4]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[C:33]([O:34]COC)=[C:32]([O:38][CH3:39])[C:31]([CH2:40][CH2:41][O:42]COC)=[C:30]([O:46]COC)[C:29]=1[O:50][CH3:51].Cl.C(=O)([O-])O.[Na+].O=O>O1CCCC1.C(O)(C)C.CO.C1C=CC=CC=1.O1CCCC1.C(O)(C)C>[CH3:1][O:2][C:3]1[C:8](=[O:9])[C:7]([CH2:13][CH2:14][CH2:15][CH3:16])=[C:6]([O:17][CH3:18])[C:5](=[O:19])[C:4]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[C:33](=[O:34])[C:32]([O:38][CH3:39])=[C:31]([CH2:40][CH2:41][OH:42])[C:30](=[O:46])[C:29]=1[O:50][CH3:51]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 516892Sodium BicarbonateHCID 197572401-[2,5-Dimethoxy-4-butyl-3,6-bis(methoxymethoxy)phenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-(2-methoxymethyloxyethyl)phenyl]pentane

Product 1

HCID 197571941-(2,5-Dimethoxy-6-butyl-1,4-benzoquinone-3-yl)-5-[2,5-dimethoxy-6-(2-hydroxyethyl)-1,4-benzoquinon-3-yl]pentane

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

520 Milligrams of 1-[2,5-dimethoxy-4-butyl-3,6-bis(methoxymethoxy)phenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-(2-methoxymethyloxyethyl)phenyl]pentane was dissolved in 5 ml of tetrahydrofuran with 5 ml of isopropanol, to this solution was added 1 milliliter of tetrahydrofuran-isopropanol (1:1) solution of 20%-hydrogen chloride, and the whole mixture was stirred at room temperature for 12 hours. After concentrated the reaction mixture, the residue obtained was treated by an azeotrotic distillation with benzene, then dissolved in 8 ml of methanol, further a small amount of sodium hydrogen carbonate was added thereto, and oxygen gas was blown into the solution for 2 hours. This solution was concentrated, and 50 ml of dichloromethane was added to the residue and the solution was washed with water and with a saturated sodium chloride aqueous solution, and concentrated. Then this product was purified by means column chromatography (diameter 2 cm×length 10 cm, adsorbent: "Silica gel 60" manufacture by E. Merck A. G., developing solvent: 30% ethyl acetate-n-hexane) to obtain 231 mg of 1-(2,5-dimethoxy-6-butyl-1,4-benzoquinone-3-yl)-5-[2,5-dimethoxy-6-(2-hydroxyethyl)-1,4-benzoquinon- 3-yl]pentane. Amorphous powdery substance.

Workup

  1. concentrationAfter concentrated the reaction mixture
  2. customthe residue obtained
  3. concentrationThis solution was concentrated
  4. addition50 ml of dichloromethane was added to the residue
  5. washthe solution was washed with water and with a saturated sodium chloride aqueous solution
  6. concentrationconcentrated
  7. customThen this product was purified by means column chromatography (diameter 2 cm×length 10 cm, adsorbent

Sources & evidence

ORD record
ord-b5534655b5094a698ea01a21826e03f4
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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