HCID 20277060, compound → HCID 20277073, compound

HRID 1248606Notes

Reaction equation

HRID 1248606 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[C:5]([C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[C:3]=1[OH:4]>C(OCC)C>[CH3:1][C:2]1[C:3](=[O:4])[C:5]([C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[C:6]([CH3:11])[C:7](=[O:10])[C:8]=1[CH3:9]

Participants

3

Reactant 1

HCID 20277060HCID 20277060, compound

Product 1

HCID 20277073HCID 20277073, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,3,5-trimethyl-6-(6'-hydroxy-1'-oxohexyl)-hydroquinone (formula III-1 wherein R=H3C, X=Y=OH, n=4, in the free form) (0.1 part) in diethyl ether (10 volume parts) was stirred with 3% aqueous ferric chloride solution at room temperature for 2 hours. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer and diethyl ether extract were washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuo to dryness. The residue was subjected to chromatography on silica gel and eluted with diethyl ether to give 2,3,5-trimethyl-6-(6'-hydroxy-1'-oxohexyl)-1,4-benzoquinone (formula IV-1 wherein R=H3C, n=4, in the free form) (0.088 part) as a yellow oil.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. extractionThe combined organic layer and diethyl ether extract
  4. washwere washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo to dryness
  7. washeluted with diethyl ether

Sources & evidence

ORD record
ord-97cb1b1ae18046f2b870d613ac5797d7
Source dataset
uspto-grants-1985_06
Patent number
US04525361

Reaction notes

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