2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Hydroxy-7-methoxy-1-tetralone

HRID 1594774Notes

Reaction equation

Cl[C:2]1[C:3](=[O:14])[C:4]([C:12]#N)=[C:5]([C:10]#N)[C:6](=O)[C:7]=1Cl.[OH:15][C:16]1C=C2C(=C[C:25]=1[O:26][CH3:27])CCCC2>O1CCOCC1>[OH:15][C:16]1[CH:10]=[C:5]2[C:4](=[CH:12][C:25]=1[O:26][CH3:27])[C:3](=[O:14])[CH2:2][CH2:7][CH2:6]2

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 231 mg of 2,3-dichloro-5,6-dicyanobenzoquinone in 2 mL of dioxane was added dropwise over a period of 3 minutes to a stirred solution of 89 mg of 6-hydroxy-7-methoxytetralin dissolved in 5% aqueous dioxane under an atmosphere of nitrogen. The resulting solution was stirred at 25° C. under nitrogen for 3 hours. Thereafter the reaction mixture was filtered through a sintered glass funnel and the solid residue of 2,3-dichloro-5,6-dicyanodihydrobenzoquinone was washed with 2 mL of dioxane. The residue wash solution was combined with the filtrate. Thereafter the dioxane was evaporated from the combined filtrate at reduced atmospheric pressure. The resulting residue was chromatographed on a column of silica gel eluted with a solution of ethyl acetate and hexane in ratio of 1 to 1 to obtain 68 mg of known 6-hydroxy-7-methoxytetralin-1-one having m.p. 117-119° C. (lit. 117-119° C. Grethe, G. et al J Org. Chem, 1968, 33 504-508.)

Workup

filtrationThereafter the reaction mixture was filtered through a sintered glass funnel
washthe solid residue of 2,3-dichloro-5,6-dicyanodihydrobenzoquinone was washed with 2 mL of dioxane
washThe residue wash solution
customThereafter the dioxane was evaporated from the combined filtrate at reduced atmospheric pressure
customThe resulting residue was chromatographed on a column of silica gel
washeluted with a solution of ethyl acetate and hexane in ratio of 1 to 1

Sources & evidence

ORD record: ord-de0dbb2e4fc34927b0a95474935ccb6c
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284789B1

Reaction notes

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