Hydrochloric Acid → HCID 19757218, compound

HRID 1588172Notes

Reaction equation

HRID 1588172 reaction equation
C[O:2][C:3]1[C:8](=[O:9])[CH:7]=[C:6]([O:10]C)[C:5](=[O:12])[C:4]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[C:19](=[O:29])[C:20]([O:27]C)=[CH:21][C:22](=[O:26])[C:23]=1[O:24]C.[OH-].[Na+].Cl>CO>[OH:29][C:19]1[C:20](=[O:27])[CH:21]=[C:22]([OH:26])[C:23](=[O:24])[C:18]=1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:4]1[C:3](=[O:2])[C:8]([OH:9])=[CH:7][C:6](=[O:10])[C:5]=1[OH:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13646077HCID 13646077, compound

Product 1

HCID 19757218HCID 19757218, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

Milligrams of 2,2'-pentamethylenebis(3,6-dimethoxy-1,4-benzoquinone) dissolved in 7 ml of methanol, was treated with 2N-sodium hydroxide, and then warmed at about 90° C. for 30 minutes. After cooling, the solution was adjusted to pH 3 with 6N-hydrochloric acid, and extracted with the mixed solvent of 150 ml of ethyl acetate-ethyl ether (1:1). The organic layer was washed twice with water and twice with an aqueous solution saturated with sodium chloride, and concentrated under reduced pressure to give 203 mg of 2,2'-pentamethylenebis(3,6-dihydroxy-1,4-benzoquinone). Yellow powdery substance.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with the mixed solvent of 150 ml of ethyl acetate-ethyl ether (1:1)
  3. washThe organic layer was washed twice with water and twice with an aqueous solution saturated with sodium chloride
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e4e8f086aae84b1b8d04c91e865674a3
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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