Acetate → HCID 20277071, compound

HRID 1390579Notes

Reaction equation

HRID 1390579 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 2N 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-bcb63228d7e048d581eba5adaaf4182d
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

Loading…