Hydrogen Peroxide → 6-chloro-2,3-dihydroxy-1,4-naphthoquinone

HRID 127177Notes

Reaction equation

HRID 127177 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([OH:13])=[CH:6][C:5]2=[O:14].C(=O)(O)[O-:16].[Na+].OO>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([OH:13])=[C:6]([OH:16])[C:5]2=[O:14]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 178516608HCID 178516608, compound

Product 1

HCID 1356252826-chloro-2,3-dihydroxy-1,4-naphthoquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.2 gm 6- chloro-2-hydroxy-1,4-naphthoquinone (or 7-chloro or mixture thereof) and 0.48 g sodium bicarbonate in 58 ml of water is cooled to 5° C. and 2.3 ml of 30% hydrogen peroxide is added in one portion. The mixture is then stirred at 22° C. for 16 hours where the red crystalline product (0.24 g) is removed by filtration and crystallized from water:methanol (2:1) giving the 6-chloro-2,3-dihydroxy-1,4-naphthoquinone, m.p. 228°-229° C.

Workup

  1. customis removed by filtration
  2. customcrystallized from water:methanol (2:1)

Sources & evidence

ORD record
ord-8724fdce033847e886547ac07f74c75e
Source dataset
uspto-grants-1981_03
Patent number
US04255405

Reaction notes

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