Hydrochloric Acid → HCID 20478610, compound

HRID 904716Notes

Reaction equation

HRID 904716 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].P(Cl)(Cl)(Cl)=O.O.O.Cl[Sn]Cl.[CH3:18][O:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[C:28](=[O:30])[CH:27]=[CH:26][C:25]2=O.Cl>C(#N)C>[CH2:1]([O:7][C:25]1[C:24]2[C:29](=[C:20]([O:19][CH3:18])[CH:21]=[CH:22][CH:23]=2)[C:28]([OH:30])=[CH:27][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81031-HexanolHCID 24813Phosphorus oxychlorideHCID 61436Stannous chloride dihydrateHCID 1232201,4-Naphthalenedione, 5-methoxy-

Product 1

HCID 20478610HCID 20478610, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10 ml of hexyl alcohol and 50 ml of acetonitrile were placed in a 1 l three-necked flask, and 12.8 g of phosphorus oxychloride was dropwisely added thereto under cooling with ice while stirring. Thereafter, 9.5 g of SnCl2.2H2O was added to the reaction mixture at room temperature. Then, 7.5 g of 8-methoxy-1,4-naphthoquinone was added to the reaction mixture at room temperature. The reaction mixture was refluxed for 2 hours on steam bath. The reaction mixture was poured into 1.2 l of diluted hydrochloric acid and extracted with 500 ml of ethyl acetate. The ethyl acetate solution was washed with water, dried with MgSO4 overnight, and concentrated under reduced pressure to obtain 9 g of oily substance. The oily substance was purified by column chromatography using a mixed solvent of n-hexane and ethyl acetate and, then, recrystallized from benzene to obtain 6 g of white crystals having a melting point of 105° to 107° C.

Workup

  1. temperatureunder cooling with ice
  2. temperatureThe reaction mixture was refluxed for 2 hours on steam bath
  3. extractionextracted with 500 ml of ethyl acetate
  4. washThe ethyl acetate solution was washed with water
  5. dry with materialdried with MgSO4 overnight
  6. concentrationconcentrated under reduced pressure
  7. customto obtain 9 g of oily substance
  8. customThe oily substance was purified by column chromatography
  9. customrecrystallized from benzene

Sources & evidence

ORD record
ord-e9b4490b1eac40ab91fd848eb9bd7823
Source dataset
uspto-grants-1983_12
Patent number
US04419439

Reaction notes

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