Diethyl Ether → HCID 12881470, compound

HRID 1248603Notes

Reaction equation

HRID 1248603 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[CH:11]([OH:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].[O]N(S(=O)([O-])=O)S(=O)([O-])=[O:22].[K+].[K+].C(OCC)C>CN(C)C=O.O>[CH3:8][C:7]1[C:2](=[O:1])[C:3]([CH:11]([OH:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH3:10])[C:5](=[O:22])[C:6]=1[CH3:9]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 3032624Potassium nitrosodisulfonateHCID 12906145HCID 12906145, compound

Product 1

HCID 12881470HCID 12881470, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2'-hydroxy-3',4',6'-trimethylphenyl)-1,6-hexanediol (formula III-3 wherein R=H3C, X=H, Y=OH, n=4 in the free form) (0.32 part) in dimethyl formamide (20 volume parts) was added all at once a mixture of Fremy's salt (0.5 part) and potassium biphosphate (0.5 part) in water (50 volume parts). The mixture was stirred for 3 hours at room temperature. The reaction product was taken up with diethyl ether. The diethyl ether 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 ethyl acetate-diethyl ether (4:1) to give 2,3,5-trimethyl-6-(1',6'-dihydroxyhexyl)-1,4-benzoquinone (formula IV-3 wherein R=H3C, n=4, in the free form) (0.26 part) as a yellow oil.

Workup

  1. washThe diethyl ether layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe residue upon removal of the solvent
  4. washeluted with ethyl acetate-diethyl ether (4:1)

Sources & evidence

ORD record
ord-1ffd8b8bc10c4769a49b925c6a871d1a
Source dataset
uspto-grants-1985_06
Patent number
US04525361

Reaction notes

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