Hydrochloric Acid → 2,3-Dibutoxy-6-chloronaphthalene-1,4-dione

HRID 325663Notes

Reaction equation

HRID 325663 reaction equation
Cl[C:2]1[C:3](=[O:15])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Cl)=[CH:8][C:7]([Cl:14])=[CH:6][CH:5]=2.Cl>CN(C)C=O>[CH2:10]([O:13][C:2]1[C:3](=[O:15])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1[O:15][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][C:7]([Cl:14])=[CH:6][CH:5]=2)[CH2:9][CH2:8][CH3:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 126602492,3,6-Trichloronaphthalene-1,4-dione

Product 1

HCID 136603762,3-Dibutoxy-6-chloronaphthalene-1,4-dioneYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium-n-butoxide (25.8 g) in dry dimethylformamide (125 ml) was added 2,3,6-trichloro-1,4-naphthoquinone (28 g) in one amount. The mixture was refluxed for 2 hours, then cooled, acidified with 6 M hydrochloric acid and evaporated. The residue was chromatographed over silica gel using dichloromethane as eluant to yield 2,3-di-n-butoxy-6-chloro-1,4-naphthoquinone (12.3 g) as a red oily solid.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-84a1761384154a5fa1de369b7e126a49
Source dataset
uspto-grants-1984_04
Patent number
US04442127

Reaction notes

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