Hydrochloric Acid → HCID 20277061, compound

HRID 647060Notes

Reaction equation

HRID 647060 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:10](=[O:27])[C:11]([CH2:19][CH2:20][CH2:21][C:22](OCC)=[O:23])=[C:12]([CH3:18])[C:13](=[O:17])[C:14]=1[O:15][CH3:16].Cl>C(OCC)C>[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[C:13]([OH:17])[C:12]([CH3:18])=[C:11]([CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[C:10]=1[OH:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12824088HCID 12824088, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20277061HCID 20277061, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a well stirred solution of lithium aluminum hydride (0.5 part) in diethyl ether (5 volume parts) was added a solution of 2,3-dimethoxy-5-methyl-6-(3'-ethoxycarbonylpropyl)-1,4-benzoquinone (formula I-2 wherein R=H3CO, n=2, in the form of ethyl ester) (0.78 part) in diethyl ether (10 volume parts) under cooling in ice-bath. After stirring at room temperature for 1 hour, the mixture was acidified with dilute hydrochloric acid. The diethyl ether layer was separated and the aqueous layer was extracted with diethyl ether. The combined diethyl ether and extract were washed with water, dried over anhydrous sodium sulfate. The diethyl ether was removed in vacuo to give 2,3-dimethoxy-5-methyl-6-(4'-hydroxybutyl)-hydroquinone (formula III-2 wherein R=H3CO, n=2, in the free form). A solution of the above product in diethyl ether was shaken with 16% aqueous ferric chloride (10 volume parts). The diethyl ether layer was separated, washed with water and dried over anhydrous sodium sulfate. The residue upon removal of the solvent was subjected to chromatography on silica gel and eluted with chloroform to give 2,3-dimethoxy-5-methyl-6-(4'-hydroxybutyl)-1,4-benzoquinone (formula IV-2 wherein R=H3Co, n=2, in the free form) (0.52 part) as an orange oil.

Workup

  1. customThe diethyl ether layer was separated
  2. extractionthe aqueous layer was extracted with diethyl ether
  3. extractionThe combined diethyl ether and extract
  4. washwere washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe diethyl ether was removed in vacuo

Sources & evidence

ORD record
ord-0278c1176a3f447987f7eb6866bd694d
Source dataset
uspto-grants-1983_10
Patent number
US04407757

Reaction notes

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