1,4-Naphthoquinone → 1,4-Naphthalenediol

HRID 2393176Notes

Reaction equation

HRID 2393176 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1>C(O)C.Cl>[CH:7]1[CH:6]=[C:5]2[C:4]([OH:11])=[CH:3][CH:2]=[C:1]([OH:12])[C:10]2=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 85301,4-Naphthoquinone

Product 1

HCID 113051,4-NaphthalenediolYield 71.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To 1,4-naphthoquinone (25 g) suspended in ethanol (100 ml) was added a solution (150 ml) of stannous chloride (368 g) in concentrated hydrochloric acid gradually at room temperature. After the evolution of heat had ceased and a homogeneous state was established, the reaction mixture was brought back to room temperature and the resulting crystals were collected by filtration, rinsed with water, and dried to provide the title compound (18.2 g).

Workup

  1. temperatureAfter the evolution of heat
  2. customwas brought back to room temperature
  3. filtrationthe resulting crystals were collected by filtration
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-d60562a1987a49baba5332b85963610f
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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