6-Chloronaphthalen-1-ol → 6-Chloronaphthalene-1,2-dione

HRID 1665266Notes

Reaction equation

HRID 1665266 reaction equation
C1(C([O:9]C(C2C=CC=CC=2)=[Se])=[Se])C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([OH:29])=[CH:24][CH:23]=[CH:22]2>O1CCCC1>[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[C:24](=[O:9])[CH:23]=[CH:22]2

Participants

4

Reactant 2

HCID 132157076-Chloronaphthalen-1-olHCID 86588323O-(benzenecarbonoselenoyl) benzenecarboselenoate

Product 1

HCID 203740386-Chloronaphthalene-1,2-dioneYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of benzeneselenic anhydride (3.18 g, 8.8 mmol) in tetrahydrofuran (30 ml), which had been heated to 70° C. was added a solution of 6-chloro-1-naphthol (1.5 g, 8.4 mmol) in tetrahydrofuran (5 ml). The reaction was maintained at 70° C. for 15 minutes. The mixture was then concentrated under reduced pressure. The residue was suspended in hexanes (100 ml) and filtered. This was repeated 5 times. The residue was dissolved in dichloromethane (100 ml), filtered and concentrated under reduced pressure to afford the product as an orange solid (1.33 g, 82%); 400 MHz 1H NMR (CDCl3) δ: 8.06 (d, J=8.4 Hz, 1H), 7.49 (dd, J=2 and 8.4 Hz, 1H), 7.41-7.38 (m, 2H), 6.50 (d, J=10 Hz, 1H).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. filtrationfiltered
  3. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0deb652d776842829d3c78371d60e6d1
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

Loading…