Chloroform → HCID 10680230, compound

HRID 2260375Notes

Reaction equation

HRID 2260375 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:16])[C:5]2[CH2:6][CH:7]=[C:8](C)[CH:9]([CH3:14])[C:10]=2[C:11](=[O:13])[CH:12]=1.[K+].[Br-].[CH:19](Cl)(Cl)Cl>O=[Mn]=O>[CH3:1][O:2][C:3]1[C:4](=[O:16])[C:5]2[C:10]([C:11](=[O:13])[CH:12]=1)=[C:9]([CH3:14])[CH:8]=[C:7]([CH3:19])[CH:6]=2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 253877Potassium BromideHCID 19710561HCID 19710561, compound

Product 1

HCID 10680230HCID 10680230, compound

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst2×

Procedure

To a solution of 5,8-dihydro-2-methoxy-5,6-dimethylnaphthalene-1,4-dione (4.00 g, 18.3 mmol) in CHCl3 (150 mL), there was added MnO2 (9.49 g, 110 mmol, Fluka). The stirred suspension was heated at reflux and monitored by 1H NMR (filtered aliquot through celite and removed solvent in vacuo). After 4.5 h, an additional portion of MnO2 (4.8 g, 55 mmol) was added and the reaction was allowed to reflux for an additional 3 h (7.5 h total). The reaction was allowed to stir overnight at rt and was filtered through Celite. The pad was washed with CHCl3 (3×30 mL). Solvent removal yielded a yellow powder (3.80 g, 95%, pure by TLC and 1H NMR); mp 146°-148° C.; 1H NMR (CDCl3) δ2.43 (s, 3H), 2.71 (s, 3H), 3.87 (s, 3H), 6.07 (s, 1H), 7.33 (s, 1H), 7.87 (s, 1H); IR (KBr) 3070 (w), 2982 (w), 2968 (w), 2946 (w), 2926 (w), 2850 (w), 1676 (s), 1646 (s), 1636 (s), 1619 (s), 1601 (s), 1247 (s), 1243 (s), 1236 (s), 1105 (s), 865 (m), 705 (m). Crystallization from EtOH yielded yellow needles (mp 147.5°-149° C.).

Workup

  1. temperatureThe stirred suspension was heated
  2. temperatureat reflux
  3. filtrationfiltered aliquot through celite
  4. customremoved solvent in vacuo)
  5. temperatureto reflux for an additional 3 h (7.5 h total)
  6. filtrationwas filtered through Celite
  7. washThe pad was washed with CHCl3 (3×30 mL)
  8. customSolvent removal
  9. customyielded a yellow powder (3.80 g, 95%, pure by TLC and 1H NMR)
  10. customCrystallization from EtOH yielded yellow needles (mp 147.5°-149° C.)

Sources & evidence

ORD record
ord-9abd8ccacc914ca4868ad67adca902c4
Source dataset
uspto-grants-1995_12
Patent number
US05476933

Reaction notes

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