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

HRID 1648696Notes

Reaction equation

HRID 1648696 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-498db280e62c4a00a584a06c192495ee
Source dataset
uspto-grants-1995_07
Patent number
US05436359

Reaction notes

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