Hydrochloric Acid → HCID 12824129, compound

HRID 1903419Notes

Reaction equation

HRID 1903419 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.O>[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

6

Reactant 3

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

Product 1

HCID 12824129HCID 12824129, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (740 mg) is suspended in 80 ml of dried ether, and a solution of 1.06 g of 2,3-dimethoxy-6-(12-methoxycarbonyldodecyl)-5-methyl-1,4-benzoquinone in 100 ml of dried ether is added dropwise with stirring and ice cooling. After 1.5 hours, ice water is added so as to decompose the excess lithium aluminum hydride, then acidified with hydrochloric acid and extracted with ether. The extract is washed with water and concentrated under reduced pressure. The residue is dissolved in 30 ml of methanol, a solution of 12 g of ferric chloride in 60 ml of water is added, and the mixture is stirred at room temperature for 1.5 hours. The liquid reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water and dried, and the solvent is distilled off under reduced pressure. The residue is dissolved in chloroform and subjected to silica gel column chromatography. The crystals recovered from the chloroform-ethanol (99:1) eluate are recrystallized from ether-hexane to give 727 mg of 6-(13-hydroxytridecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (in formula I, n=13) as yellow needles. m.p. 65°-66° C.

Workup

  1. extractionextracted with ether
  2. washThe extract is washed with water
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue is dissolved in 30 ml of methanol
  5. additiona solution of 12 g of ferric chloride in 60 ml of water is added
  6. stirringthe mixture is stirred at room temperature for 1.5 hours
  7. customThe liquid reaction mixture
  8. extractionextracted with ethyl acetate
  9. washThe extract is washed with water
  10. customdried
  11. distillationthe solvent is distilled off under reduced pressure
  12. dissolutionThe residue is dissolved in chloroform
  13. customThe crystals recovered from the chloroform-ethanol (99:1) eluate
  14. customare recrystallized from ether-hexane

Sources & evidence

ORD record
ord-61e6a6f7b18c47978e9a558aadea4d0f
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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