Project to develop a synthetic method for p-anisyl alcohol/Literature sources

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This page provides links to the chemical literature and databases used in this project at SUNY Potsdam. If you are joining us from another institution, please add appropriate links for your own institution, as the SUNY links will not work for outside students.

We will use primary sources (journals and dissertations) as well as secondary/tertiary sources such as books and web databases. There are two main types of chemical procedure you will look for – generic methods (for reducing aldehydes in general to the corresponding alcohol) and specific methods (for carrying out the exact reaction you want to try). We will look for both, because the generic methods (in italics) may sometimes identify a superior process, or at least help us choose a specific method.

The literature sources are given in priority order. Your task manager will assign one of these sources to you. Once your task has been assigned, begin searching immediately.

1. Chemical Abstracts “STN Easy” search results (done by scribes + moderator). This information is copyrighted and cannot be shared here.
2. ACS Journal database: One person to search before 1999, another 2000-present. This page is to be found via the SUNY Potsdam library databases page.
3. Science Direct: One person to search before 1999, another 2000-present. SUNY Potsdam library databases page
4. Organic Syntheses: One person to search for reduction on aromatic aldehydes to the corresponding alcohol
5. Books: As supplied by the library staff and the instructor. These will mostly provide generic information. No. of people to be assigned on the day.
6. Google Scholar: One person to search for the specific reaction.
7. Web search: One person to search on the given InChIKeys in Google and at least one other major search engine.
8. ChemSpider: One person to search anisaldehyde and anisyl alcohol literature
9. WebReactions: (www.webreactions.net) One person to search for reduction on aromatic aldehydes to the corresponding alcohol.

Reaction to be searched

Reactant

• Common name: p-anisaldehyde
• IUPAC name: 4-methoxybenzaldehyde
• CAS No: [123-11-5]
• InChI: InChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
• InChIKey: ZRSNZINYAWTAHE-UHFFFAOYSA-N

Product

• Common name: p-anisyl alcohol, p-methoxybenzyl alcohol
• IUPAC name: (4-methoxyphenyl)methanol
• CAS No: [105-13-5]
• InChI: InChI=1S/C8H10O2/c1-10-8-4-2-7(6-9)3-5-8/h2-5,9H,6H2,1H3
• InChIKey: MSHFRERJPWKJFX-UHFFFAOYSA-N

Final chosen methods for Thursday lab

First choice

Green procedure for the preparation of scented alcohols from carbonyl compounds. Villa, Carla; Trucchi, Beatrice; Gambaro, Raffaella; Baldassari, Sara International Journal of Cosmetic Science, 2008, 30, 139–144. DOI: 10.1111/j.1468-2494.2008.00431.x Also on Moodle, since link sometimes fails.

Second choice

• David Davidson, Marston Taylor Bogert, The Preparation of Aromatic Alcohols by the Crossed Cannizzaro Reaction with Formaldehyde. J. Am. Chem. Soc., 1935, 57(5), 905–905. DOI: 10.1021/ja01308a036

or possibly the related paper:

• Yoshizawa, K., Toyota, S. Toda, F. Solvent-free Claisen and Cannizzaro reactions. Tetrahedron Lett. 2001, 42, 7983-7985.