4-Methylanisole → p-(Dimethoxymethyl)anisole

HRID 1995771Notes

Reaction equation

HRID 1995771 reaction equation
[CH3:1][O:2]C1C=CC(C)=CC=1.[C-]#N.[Na+].[CH3:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1>>[CH3:13][O:14][CH:15]([O:2][CH3:1])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 77314-MethylanisoleHCID 8929Sodium CyanideHCID 73689p-(Methoxymethyl)anisole

Product 1

HCID 75140p-(Dimethoxymethyl)anisoleYield 15%

Procedure

In the article "Nuclear Cyanation of Methylanisoles" by K. Yoshida, M. Shigi and T. Fueno in J. Org. Chem., 1975, Vol. 40, No. 1, pp. 63-66, the reaction of 4-methoxytoluene (Ic) in a methanolic solution of NaCN or Na acetate is described. In this reaction, 4-(methoxymethyl)-anisole and, in a material (current) yield of 15% (24%) of the theoretical, anisaldehyde-dimethylacetal (IIc) are also formed, in addition to the respective ring-substitution products.

Sources & evidence

ORD record
ord-1b82e5949d2b438fa229739f9e648332
Source dataset
uspto-grants-1983_09
Patent number
US04405816

Reaction notes

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