2,5-Dimethyl-4-benzoquinone → 6-Hydroxy-4,4,5,8-tetramethylchroman-2-one

HRID 1884317Notes

Reaction equation

HRID 1884317 reaction equation
[CH3:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([CH3:9])[C:6](=[O:8])[CH:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CCOCC>[OH:8][C:6]1[C:5]([CH3:9])=[C:4]2[C:3](=[C:2]([CH3:1])[CH:7]=1)[O:10][C:6](=[O:8])[CH2:7][C:2]2([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 87182,5-Dimethyl-4-benzoquinoneHCID 24489Sodium Dithionite

Product 1

HCID 6132386-Hydroxy-4,4,5,8-tetramethylchroman-2-oneYield 197.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2,5-Dimethylbenzoquinone (10 g, 73.5 mmol) was dissolved in 300 mL of ether, which was mixed with an aqueous solution of sodium hydrosulfite (178 g in 150 mL of water, 85% pure, 870 mmol). The mixture was shaken until the ether layer became nearly colorless. The ether layer was separated, and the aqueous layer was extracted with ethyl ether (3×200 mL). The combined ether layers were washed with brine (2×150 mL) and dried over MgSO4. Filtration and solvent evaporation gave 10.03 g (72.6 mmol) of the hydroquinone as a white solid.

Workup

  1. customThe ether layer was separated
  2. extractionthe aqueous layer was extracted with ethyl ether (3×200 mL)
  3. washThe combined ether layers were washed with brine (2×150 mL)
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and solvent evaporation

Sources & evidence

ORD record
ord-c3e1c1803be74b0ab2884fddb9fcc169
Source dataset
uspto-grants-2004_07
Patent number
US06764768B2

Reaction notes

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