6-hydroxy-1,4-naphthoquinone → HCID 18376526, compound

HRID 2300577Notes

Reaction equation

HRID 2300577 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]=[CH:6][C:5]2=[O:13]>CO>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([C:9]([CH3:10])([CH3:4])[CH:8]=[O:12])=[CH:6][C:5]2=[O:13]

Participants

3

Reactant 1

HCID 118195036-hydroxy-1,4-naphthoquinone2×

Product 1

HCID 18376526HCID 18376526, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Hydroxynaphthoquinone (compound 2 prepared in step I above) (0.74 g, 2.35 mmol) was dissolved in 75% MeOH (30 mL) and powdered FeCl3·6H2O (1.65 g, 6.1 mmol) was added. The mixture was stirred for 4 h. The solvent was evaporated and the crude product (compound 3) was purified on silica gel with hexane:EtOAc 4:1. Yield: 0.27 g (47%). 1H NMR (400 MHz, Acetone-d6) δ 1.36 (s, 6 H), 6.90 (s, 1 H), 7.24 (dd, 1 H), 7.39 (d, 1 H), 7.94 (d, 1 H), 9.64 (s, 1 H).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product (compound 3) was purified on silica gel with hexane:EtOAc 4:1

Sources & evidence

ORD record
ord-ba99adc3743d447e9a6dd6fb00de5f82
Source dataset
uspto-grants-2002_12
Patent number
US06498182B2

Reaction notes

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