Sodium Dithionite → Anthracene-1,4-diol

HRID 2306903Notes

Reaction equation

HRID 2306903 reaction equation
[C:1]1(=[O:16])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4](=[O:15])[CH:3]=[CH:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.O1CCOCC1>[OH:15][C:4]1[C:5]2[C:14](=[CH:13][C:12]3[C:7]([CH:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:1]([OH:16])=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 694571,4-Anthraquinone

Product 1

HCID 12631814Anthracene-1,4-diolYield 832.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To 2.00 g (1.00 mmol) of 1,4-anthracenedione, a solution of 6.68 g (38.0 mmol) of sodium hydrosulfite in 50 mL of water and 50 mL of 1,4-dioxane was added. The resulting mixture was stirred at 25° C. for 3 h, and added 100 mL of water. The mixture was cooled over an ice-water bath, and the precipitated dark green solids were collected by filtration, washed twice with water, and dried under vacuum to give 1.75 g (87% yield) of 1,4-dihydroxyanthracene, mp 167-169° C.; 1H NMR d 8.70 (s, 2H, C 9,10 Hs), 8.05 (m, 2H, C 5,8 Hs), 7.50 (s, 2H, C 6,7 Hs), 6.60 (s, 2H, C 2,3 Hs).

Workup

  1. temperatureThe mixture was cooled over an ice-water bath
  2. filtrationthe precipitated dark green solids were collected by filtration
  3. washwashed twice with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-02172d876147416db46423a195d29279
Source dataset
uspto-grants-2004_12
Patent number
US06828450B2

Reaction notes

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