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

HRID 986845Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:14])[CH:6]=[C:7]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH:8]=1.Cl[CH2:16][CH2:17][C:18](Cl)([CH3:20])[CH3:19].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Ni+2]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH:11]([CH3:12])[CH3:13])[CH:6]=[C:5]2[C:4]=1[CH:16]=[CH:17][C:18]([CH3:20])([CH3:19])[O:14]2

Participants

Conditions

Temperature: 125 °C

Procedure

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%.

Workup

temperatureThe mixture is cooled
customthe solvent removed
temperatureThe mixture is heated
filtrationThe solution is filtered
customthe filtrate evaporated
customthe residue purified

Sources & evidence

ORD record: ord-948a6e785fa04c06bb2f6ceb30bb0af8
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04716238

Reaction notes

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