Hydrochloric Acid → 7-Chloro-2-methoxy-1,4-naphthoquinone

HRID 726955Notes

Reaction equation

HRID 726955 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[CH:7]=[C:8]([OH:13])[C:9]2=[O:12])=[CH:4][CH:3]=1.Cl.[CH3:16]O>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[CH:7]=[C:8]([O:13][CH3:16])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178516609HCID 178516609, compound

Product 1

HCID 150296297-Chloro-2-methoxy-1,4-naphthoquinone

Procedure

7-Chloro-2-hydroxy-1,4-naphthoquinone (0.73 g) was added to 4% (w/w) hydrogen chloride in methanol (14 mL). The solution was heated to reflux for 0.5 hour. Upon cooling to room temperature, a precipitate formed which was filtered, washed (methanol) and dried under vacuum (25° C., 15 Pa) to give an orange solid (0.72 g); 250 MHz NMR: 8.10 (d,1, J=2.2), 8.04 (d,1, J=8.3), 7.71 (dd,1, J=8.3, 2.2), 6.19 (s,1), 3.92 (s,3).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 0.5 hour
  3. customa precipitate formed which
  4. filtrationwas filtered
  5. washwashed (methanol)
  6. customdried under vacuum (25° C., 15 Pa)

Sources & evidence

ORD record
ord-bfa6fcd8eafb4218b3df43aac9596a20
Source dataset
uspto-grants-1998_01
Patent number
US05712272

Reaction notes

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