Sodium Dithionite → Anthracene-1,4-diol

HRID 1015455

Reaction equation

HRID 1015455 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].O.O1CCOCC1.[C:16]1(=[O:31])[C:29]2[C:20](=[CH:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19](=[O:30])[CH:18]=[CH:17]1>O>[OH:30][C:19]1[C:20]2[C:29](=[CH:28][C:27]3[C:22]([CH:21]=2)=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:16]([OH:31])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 694571,4-AnthraquinoneHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 12631814Anthracene-1,4-diolYield 61.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium hydrosulfite (16.70 g, 42.0 mmol, 1 molar equivalent) in a water/dioxane (3/2) (250 mL) mixture is added under nitrogen to the 1,4-anthracenedione 1a (5.00 g, 24.0 mmol, 1 molar equivalent). The resulting mixture is stirred at room temperature for 3 h. Water is added and the resulting precipitate is filtered, washed with water and dried under vacuum to give the title compound as a yellow powder (3.10 g, 61%). 1H NMR (300.13 MHz, THF-d8) (ppm) 6.53 (s, 2H) 7.34-7.40 (m, 2H) 7.96-7.99 (m, 2H) 8.65 (s, 2H) 8.70 (s, 2H).

Workup

  1. filtrationthe resulting precipitate is filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-9d255020083a43f4b0badb49bfb974f6
Source dataset
uspto-grants-2011_07
Patent number
US07985353B2

Linked notes

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