HCID 14822010, compound → HCID 13910194, compound

HRID 330551Notes

Reaction equation

HRID 330551 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[C:22](=[O:23])[C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[C:19](=[O:28])[C:18]=2[CH3:29])=[CH:7][CH:6]=1)(=O)C>Cl.CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[C:22](=[O:23])[C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[C:19](=[O:28])[C:18]=2[CH3:29])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 14822010HCID 14822010, compound

Product 1

HCID 13910194HCID 13910194, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

6-[6-(4-Acetoxyphenyl)hexyl]-2,3-dimethoxy-5-methyl-1,4-benzoquinone (2.1 g) is dissolved in a mixture of concentrated hydrochloric acid (0.3 ml) and methanol (55 ml), and the solution is allowed to stand at room temperature for 4 hours. The methanol is distilled off under reduced pressure, and the residue is diluted with water and extracted with ethyl acetate (200 ml). The extract is washed with water and dried. The solvent is then distilled off under reduced pressure and the residue is purified by silica gel column chromatography. The fractions containing the desired product are recrystallized from ether-hexane to give 830 mg of 6-[6-(4-hydroxyphenyl)hexyl]-2,3-dimethoxy-5-methyl-1,4-benzoquinone, m.p. 87°-88° C.

Workup

  1. distillationThe methanol is distilled off under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with ethyl acetate (200 ml)
  4. washThe extract is washed with water
  5. customdried
  6. distillationThe solvent is then distilled off under reduced pressure
  7. customthe residue is purified by silica gel column chromatography
  8. additionThe fractions containing the desired product
  9. customare recrystallized from ether-hexane

Sources & evidence

ORD record
ord-6bd486e0d2eb4a1fb4e147a425f27abc
Source dataset
uspto-grants-1990_01
Patent number
US04897420

Reaction notes

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