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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 986845Generated: October 30, 2026

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-Methoxy-2,2-dimethyl-7-(2-methylpropoxy)-2H-1-benzopyran

https://huagongshe.com/reaction/986845

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 6775—
Reactant1,3-Dichloro-3-methylbutaneHCID 69358—
ReactantHCID 20156634HCID 20156634—
CatalystNickel(II) acetylacetonateHCID 9834912—
Product5-Methoxy-2,2-dimethyl-7-(2-methylpropoxy)-2H-1-benzopyranHCID 18533169%

Reaction Conditions

Temperature125 °C

Reaction Steps

A mixture of 3.9 g (20 millimoles) of 3-methoxy-5-isobutoxy-phenol, 2.8 g (20 millimoles) of 1,3-dichloro-3-methyl-butane and 0.26 g (1 millimole) of bis-(acetyl-acetonato)-nickel is heated at 125° C. for 8 hours. The mixture is cooled, the solvent removed, the residue taken up in 40 ml of anhydrous benzene and 0.8 g (3.5 millimoles) of DDQ (dichloro-dicyano-benzoquinone) are added. The mixture is heated to boiling for 60 hours. The solution is filtered, the filtrate evaporated and the residue purified as described in Example 3. Thus 3.6 of the desired compound are obtained in the form of a colorless oil, yield 69%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04716238
Source datasetuspto-grants-1987_12
ORD IDord-948a6e785fa04c06bb2f6ceb30bb0af8
Source noteuspto-grants-1987_12