Thionyl Chloride → 2-Chloro-6,7-diethylnaphthalene-1,4-dione

HRID 596896Notes

Reaction equation

HRID 596896 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH2:13][CH3:14])[C:9](=[O:15])[C:8](O)=[CH:7][C:6]2=[O:17])[CH3:2].S(Cl)([Cl:20])=O>>[Cl:20][C:8]1[C:9](=[O:15])[C:10]2[C:5]([C:6](=[O:17])[CH:7]=1)=[CH:4][C:3]([CH2:1][CH3:2])=[C:12]([CH2:13][CH3:14])[CH:11]=2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178435351HCID 178435351, compound

Product 1

HCID 123664012-Chloro-6,7-diethylnaphthalene-1,4-dione

Procedure

A solution of 6,7-diethyl-2-hydroxy-1,4-naphthoquinone (22 g; 0.096 mole) in thionyl chloride (250 ml) was refluxed for 12 hours and the solvent removed in vacuo. Repeated evaporation with dry benzene gave an orange solid which after recrystallisation from ethanol in the presence of charcoal weighed 18.04 g (76%) and had m.p. 90°-92° C. (Found; C, 67.21; H, 5.39; Cl, 14.21; C14H13ClO2 requires; C, 67.61; H, 5.27; Cl, 14.26%).

Workup

  1. customthe solvent removed in vacuo
  2. customevaporation with dry benzene
  3. customgave an orange solid which
  4. customafter recrystallisation from ethanol in the presence of charcoal

Sources & evidence

ORD record
ord-bacfd51aa7fe443f82aac23b7574cec9
Source dataset
uspto-grants-1977_03
Patent number
US04012407

Reaction notes

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