1,4-Naphthoquinone → HCID 14440163, compound

HRID 1857345Notes

Reaction equation

HRID 1857345 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)(=O)C.[Pt]=O>[OH:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]([OH:12])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 85301,4-Naphthoquinone

Product 1

HCID 14440163HCID 14440163, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1,4-naphthoquinone (10 g, 63.3 mM) in glacial acetic acid were added platinum oxide (0.75 g, 3.3 mM) and the mixture was hydrogenated in a Parr apparatus under a pressure of 30-40 psi for about 24 h at room temperature. The catalyst was filtered off, the acetic acid was evaporated under vacuum, the residue was dissolved in hot water (200 ml) and the solution cooled to give crystalline 1,4-dihydroxytetralin in 58.3% yield (4.0 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe acetic acid was evaporated under vacuum
  3. dissolutionthe residue was dissolved in hot water (200 ml)
  4. temperaturethe solution cooled

Sources & evidence

ORD record
ord-4ff4f033206b434599bad496effa9b38
Source dataset
uspto-grants-2000_11
Patent number
US06147073

Reaction notes

Loading…