Benzyl Alcohol

Sandra Forbes

Product Manager

Benzyl alcohol (also known as α-cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl); thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

Natural occurrences

Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. It is also found in a variety of essential oils including jasmine, hyacinth and ylang-ylang. It is also found in castoreum from the castor sacs of beavers. Benzyl esters also occur naturally.

Recent Literature

A transition-metal- and catalyst-free hydrogenation of a wide range of aryl halides is promoted by bases using either aldehydes or alcohols as hydrogen source. One equivalent of benzaldehyde affords an equal yield as that of 0.5 equiv of benzyl alcohol. The kinetic study reveals that the initial rate of PhCHO is nearly 4 times faster than that of BnOH. Radical trapping experiments indicate the radical nature of this reaction.

H.-X. Zheng, X.-H. Shan, J.-P. Qu, Y.-B. Kang, Org. Lett., 2017, 19, 5114-5117. 10.1021/acs.orglett.7b02399

A simple ruthenium catalyst achives a semihydrogenation of diaryl alkynes to the corresponding E-alkenes in very good yields using alcohols as the hydrogen source. Best results were obtained using benzyl alcohol as the hydrogen donor, although biorenewable alcohols such as furfuryl alcohol could also be applied.

A. Ekebergh, R. Begon, N. Kann, J. Org. Chem., 2020, 85, 2966-2975. 10.1021/acs.joc.9b02721

Quoted from: https://www.organic-chemistry.org/chemicals/reductions/benzyl-alcohol.shtm

Aladdinsci: https://www.aladdinsci.com/