Sodium Dithionite → 6-(10-Acetoxydecyl)-2,3-dimethoxy-5-methylhydroquinone

HRID 1734935Notes

Reaction equation

HRID 1734935 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[C:28](=[O:29])[C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[C:25](=[O:34])[C:24]=1[CH3:35])(=[O:11])[CH3:10]>CCOCC.O>[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[C:28]([OH:29])=[C:27]([O:30][CH3:31])[C:26]([O:32][CH3:33])=[C:25]([OH:34])[C:24]=1[CH3:35])(=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 110902052-(10-(Acetyloxy)decyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

Product 1

HCID 152949936-(10-Acetoxydecyl)-2,3-dimethoxy-5-methylhydroquinone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

2,3-Dimethoxy-6-(10-hydroxydecyl)-5-methyl-1,4-benzoquinone (3.38 g) was dissolved in dichloromethane (50 ml). Pyridine (1 ml) was added, and acetyl chloride (0.8 ml) was added with stirring under ice-cooling. After stirring for 1 hour at the same temperature, the mixture was washed with 0.1N hydrochloric acid (50 ml) followed by water (50 ml). The dichloromethane layer was concentrated under reduced pressure to obtain 6-(10-acetoxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone as a red oil. This oil was dissolved in ether (50 ml), and a solution of sodium hydrosulfite (4 g) in water (50 ml) was added. Stirring was continued at room temperature until the red color of the ether layer disappeared. The ether layer was separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the desired compound (3.8 g) as a pale yellow oil.

Workup

  1. customThe ether layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98d1e31196eb48ee9a0b1737bd8f58b2
Source dataset
uspto-grants-1996_07
Patent number
US05534639

Reaction notes

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