2-(10-(Acetyloxy)decyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione → Idebenone

HRID 1762354Notes

Reaction equation

HRID 1762354 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[C:20](=[O:21])[C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[C:17](=[O:26])[C:16]=1[CH3:27])(=O)C>Cl.CO>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[C:20](=[O:21])[C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[C:17](=[O:26])[C:16]=1[CH3:27]

Participants

4

Reactant 1

HCID 110902052-(10-(Acetyloxy)decyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

Product 1

HCID 3686IdebenoneYield 59.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

In a mixture of 0.04 ml of concentrated hydrochloric acid and 11 ml of methanol was dissolved 216 mg of 6-(10-acetoxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone, and the solution was left standing overnight at room temperature. The reaction solution was concentrated under reduced pressure and the concentrate was diluted with water, which was subjected to extraction with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, then dried. The solvent was evaporated under reduced pressure. The residue was recrystallized from hexane-ethylacetate to yield 115 mg of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone as orange-colored needles, m.p. 52°-53° C.

Workup

  1. waitthe solution was left
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionthe concentrate was diluted with water, which
  4. extractionwas subjected to extraction with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. customdried
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was recrystallized from hexane-ethylacetate

Sources & evidence

ORD record
ord-39f59db1bf92473e827a3bd308350040
Source dataset
uspto-grants-1989_05
Patent number
US04831265

Reaction notes

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