1,3-Dimethoxybenzene → 3,5-Dimethoxytoluene

HRID 2295708Notes

Reaction equation

HRID 2295708 reaction equation
[C:1]1(=O)CCCC(=O)C1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1.CC1CC(=O)CC(=O)C1>>[CH3:9][O:10][C:11]1[CH:16]=[C:15]([CH3:1])[CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1

Participants

4

Reactant 3

HCID 90251,3-DimethoxybenzeneHCID 104341,3-CyclohexanedioneHCID 4580955-Methylcyclohexane-1,3-dione

Product 1

HCID 778443,5-DimethoxytolueneYield 60%

Procedure

In contrast cyclohexane-1,3-dione (R2 to R4 are H), for example, can be converted in 76% yield, to 1,3-dimethoxybenzene of type Ic over a Cu2O/thionyl chloride catalyst in methanolic solution. A 60% yield of 1,3-dimethoxy-5-methyl-benzene is obtained as the main product from 5-methyl-cyclohexane-1,3-dione under the same conditions.

Sources & evidence

ORD record
ord-64c14d6b03f84413a38c3ab9a3018583
Source dataset
uspto-grants-1984_01
Patent number
US04426332

Reaction notes

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