How can I make phenethyl alcohol $(\ce{C6H5CH2CH2OH})$ from benzene?

I have got information that phenethyl alcohol is made from benzene by Friedel-Crafts reaction between benzene and ethylene oxide in the presence of aluminium trichloride as follows:

$$\ce{C6H6 + CH2CH2O + AlCl3 → C6H5CH2CH2OAlCl2 + HCl}$$

But I have no idea how it reacts and proceeds to work.

Can anyone help me understanding the mechanism of synthesis and reaction of making phenethyl alcohol from benzene?


1 Answer 1


$\ce{AlCl3}$ is a Lewis acid and will bind to the oxygen of the ethylene oxide giving a species that functions as $\ce{[R2O-AlCl2]+}.$

This cationic species will be attacked at carbon by the electron-rich aromatic ring in much the same way as a standard Friedel-Crafts reaction intermediate generated from an alkyl halide to give $\ce{[Ph-CH2CH2-OAlCl2]+}.$ This then loses $\ce{HCl}$ to give $\ce{PhCH2CHOAlCl2}$ which is stable until aqueous workup which gives phenethyl alcohol.

  • $\begingroup$ I can understand well about the mechanism of making phenethyl alcohol and how it works as Friedel-crafts reaction with Lewis acid and and make alkyl benzene! $\endgroup$
    – Jan
    Jul 12, 2019 at 15:58

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