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I'm looking to synthesize salicylic acid in my school laboratory for an investigatory project. The Kolbe's reaction looks promising:

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Any suggestions on where to get the $\ce{CO2}$ from? Will the reaction of vinegar + $\ce{NaHCO3}$ be okay? Does this reaction need a suitable temperature and/or catalysts? I tried to search for similar experiments but the others usually use reagents and catalysts inaccessible to me.

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    $\begingroup$ Do you have access to solid CO2 (dry ice)? $\endgroup$
    – Waylander
    Commented Jul 4, 2023 at 6:23
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    $\begingroup$ According to Wikipedia, the reaction is performed at CO2 pressure 100 atm. It may not be a suitable scenario for safety reasons. $\endgroup$
    – Poutnik
    Commented Jul 4, 2023 at 7:40
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    $\begingroup$ Reimer-Tiemann followed by oxidation may be more achievable in a school lab en.wikipedia.org/wiki/Reimer%E2%80%93Tiemann_reaction see procedure orgsyn.org/demo.aspx?prep=CV3P0463 $\endgroup$
    – Waylander
    Commented Jul 4, 2023 at 10:27
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    $\begingroup$ @AdityaKumarPanda then look at the R-T procedure which is done with hydroxide and chloroform as IMO you will struggle to get a high enough concentration of CO2 in your reaction mixture. $\endgroup$
    – Waylander
    Commented Jul 4, 2023 at 14:34
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    $\begingroup$ @GauravSaiMaddipati see my answer below $\endgroup$
    – Waylander
    Commented Feb 5 at 10:02

2 Answers 2

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Riemer and Tiemann originally reported that using carbon tetrachloride in place of chloroform gives salicylic acid as major product plus p-hydroxybenzoic acid. It is mentioned in this review by Wynberg here and this Indian Journal of Chemistry paper here which has experimental conditions. This seems to have received little attention (which is why I was initially unaware of it), possibly because yields appear low. Other researchers report that the para product predominates (see the Indian Journal of Chem paper). The catalytic effect of copper metal in giving the para isomer was reported here

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Dissolve phenol in a solution of sodium hydroxide (NaOH) and water. Pass carbon dioxide (CO2) gas through the solution while keeping it cool in an ice bath. This forms sodium salicylate. Acidify the solution with dilute sulfuric acid (H2SO4) to precipitate salicylic acid. Filter and wash the resulting salicylic acid crystals. Purify the product by recrystallization if necessary.

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  • $\begingroup$ This will work PROVIDED you have a good source of CO2 - either compressed gas or dry ice. The OP does not. $\endgroup$
    – Waylander
    Commented Feb 5 at 12:01
  • $\begingroup$ Does this work well at normal pressures? $\endgroup$
    – matt_black
    Commented Feb 5 at 12:49

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