Hydrochloric Acid → HCID 12824129, compound

HRID 637884Notes

Reaction equation

HRID 637884 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:10](=[O:35])[C:11]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](OC)=[O:32])=[C:12]([CH3:18])[C:13](=[O:17])[C:14]=1[O:15][CH3:16].Cl>CCOCC>[OH:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:11]1[C:10](=[O:35])[C:9]([O:8][CH3:7])=[C:14]([O:15][CH3:16])[C:13](=[O:17])[C:12]=1[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12824087HCID 12824087, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 12824129HCID 12824129, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (740 mg) is suspended in dry ether (80 ml) and to the suspension is added dropwise a solution of 2,3-dimethoxy-5-methyl-6-(12-methoxycarbonyldodecyl)-1,4-benzoquinone (1.06 g) in dry ether (100 ml) under ice-cooling and stirring. After 1.5 hour, ice-water is added to the mixture to decompose excess lithium aluminum hydride. The mixture is acidified with hydrochloric acid and subjected to extraction with ether. The extract is washed with water and concentrated under a reduced pressure. The residue is dissolved in methanol (30 ml) and to the solution is added a solution of ferric chloride (12 g) in water (60 ml) and the mixture is stirred at room temperature for 1.5 hour. The reaction mixture is diluted with water and subjected to extraction with ethyl acetate. The extract is washed with water, and dried. The solvent is distilled off under reduced pressure. The residue is dissolved in chloroform and subjected to column chromatography on silica gel. The crystals obtained from the first-emerging fraction eluted with chloroformethanol (99:1) is recrystallized from ether-hexane. The above procedure yields 6-(13-hydroxytridecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone as yellow needles. (727 mg) Melting point 65°-66° C.

Workup

  1. temperaturecooling
  2. extractionsubjected to extraction with ether
  3. washThe extract is washed with water
  4. concentrationconcentrated under a reduced pressure
  5. dissolutionThe residue is dissolved in methanol (30 ml) and to the solution
  6. additionis added a solution of ferric chloride (12 g) in water (60 ml)
  7. stirringthe mixture is stirred at room temperature for 1.5 hour
  8. additionThe reaction mixture is diluted with water
  9. extractionsubjected to extraction with ethyl acetate
  10. washThe extract is washed with water
  11. customdried
  12. distillationThe solvent is distilled off under reduced pressure
  13. dissolutionThe residue is dissolved in chloroform
  14. customThe crystals obtained from the first-emerging fraction
  15. washeluted with chloroformethanol (99:1)
  16. customis recrystallized from ether-hexane

Sources & evidence

ORD record
ord-a8e6db2e907641e4b4fb75ad05d1f11f
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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