Acetate → HCID 20277071, compound

HRID 1679861Notes

Reaction equation

HRID 1679861 reaction equation
[CH3:1][C:2]1[C:3](=[O:22])[C:4]([C:11](=[O:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:20])[CH3:19])=[C:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].C([O-])(=O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+]>CO>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[C:5]([CH3:10])=[C:4]([C:11](=[O:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:20])[CH3:19])[C:3]=1[OH:22]

Participants

6

Reactant 4

HCID 175AcetateHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 12906159HCID 12906159, compound

Product 1

HCID 20277071HCID 20277071, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 2,3,5-trimethyl-6-(6'-acetoxy-1'-oxohexyl)-1,4-benzoquinone (formula IV-1 wherein R=H3C, n=4, in the form of acetate ) (0.5 part), sodium hydrosulfite (1 part) and 30% aqueous methanol (20 volume parts) was added dropwise 2 N aqueous sodium hydroxide (1.6 volume part) at 5° C. The mixture was allowed to stand for 3 hours at the same temperature. After removal of the methanol and acidification with phosphoric acid, the product was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was subjected to chromatography on silica gel and eluted with ethyl acetate to give 2,3,5-trimethyl-6(6'-acetoxy-1'-oxohexyl)hydroquinone (formula III-1 wherein R=H3C, X=Y=OH, n=4, in the form of acetate) (0.075 part). Further elution with the same solvent gave 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) (0.265 part).

Workup

  1. customAfter removal of the methanol and acidification with phosphoric acid
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-aa2f9b1c862a483aa8a1f535a37edef1
Source dataset
uspto-grants-1981_06
Patent number
US04271083

Reaction notes

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