[cristiro]

This is my school homework: synthesis of the compound p-methoxybenzyl chloride . I can manage myself. Any help wellcomed. Thank you

[Garneck]

I can manage myself.

Well then - good luck.

[sundberg]

Hehe.
Well, if you want us to help you you better give us some more information. Are you just looking for general synthetic procedures, or do we have a specific starting compound to work with?

[cristiro]

The synthesys should be started from simpler aromatic structure like benzene , toluene.

[ksr985]

try chloroformylation of anisole

[cristiro]

This is a good one. Do you know another synthesys?

[ksr985]

this is probably a better method than chlorinating a substituted toluene. that might lead to polysubstituted products. try scifinder for reaction conditions and yield.

[cristiro]

What is meant by chloroformylation? Anisol should be treated with  chloroform or you refer to vilsmeier reaction? Anyone who knows?

[ethylacetate]

anisole,
p-methoxybenzaldehyde,
p-methoxybenzalchol,
p-methoxybenzyl chloride

[lavoisier]

I guess ksr985 meant chloromethylation, i.e.:

Ar-H + CH2O + HCl --> Ar-CH2-Cl + H2O (catalysts = ZnCl2...)

which yields the product in one step from anisole. Here you could still have byproducts (ortho-, polysubstitution).

[cristiro]

p-Methoxybenzyl chloride  was prepared from 324 g. (3 moles) of anisole and 303 ml. of a 40% solution of formaldehyde
(representing 4 moles of formaldehyde) by saturation of the mixture at -5 C to -2 C with
dry hydrogen chloride within three hours. An initially formed colorless gelatinous suspension
was dissolved again as saturation proceeded. The mixture was then poured onto
ice and the oily layer was separated, dried over calcium chloride, and then fractionated
at 16 mmHg. After a forerun (b.p. 60-110 C) of about 40 ml., 220 g. (47%) of a colorless oil, b.p. 115-120 C, was obtained, while 150 g. of higher-boiling material was left behind.