Ethanol → HCID 12824119, compound

HRID 1390586Notes

Reaction equation

HRID 1390586 reaction equation
[CH3:1][C:2]1[C:3](=[O:19])[C:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].O.[CH2:21](O)[CH3:22]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:3](=[O:19])[C:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:21][CH3:22])=[O:17])=[C:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 129061502,3,5-Trimethyl-6-(5'-carboxypentyl)-1,4-benzoquinone

Product 1

HCID 12824119HCID 12824119, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a well stirred solution of 2,3,5-trimethyl-6-(5'-carboxypentyl)-1,4-benzoquinone (formula I-2 wherein R=H3C, n=4, in the free form) (0.21 part) in ethanol (10 volume parts) was added 3 drops of concentrated sulfuric acid under cooling in ice bath and kept standing for 12 hours. After addition of water, the reaction mixture was extracted with diethyl ether and the diethylether layer was 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 2,3,5-trimethyl-6-(5'-ethoxycarbonylpentyl)-1,4-benzoquinone (formula I-2 wherein R=H3C, n=4, in the form of ethyl ester) (0.20 part) as an orange oil.

Workup

  1. temperatureunder cooling in ice bath
  2. extractionthe reaction mixture was extracted with diethyl ether
  3. washthe diethylether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue upon removal of the solvent
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-86557230a8ca4c0f99afdf2f372ac48c
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

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