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Benzyl Alcohol and Benzoic Acid from Benzaldehyde and Strong Potash (Cannizzaro, Gattermann 1914)
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4. Ugushyingo 2026DE
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Benzyl Alcohol and Benzoic Acid from Benzaldehyde and Strong Potash (Cannizzaro, Gattermann 1914)

Strong potash splits benzaldehyde in two: half is reduced to benzyl alcohol, half oxidised to benzoic acid (as potassium benzoate). 20 g of benzaldehyde gives about 8 g of benzyl alcohol, boiling at 206 °C; the benzoic acid is thrown down with hydrochloric acid. Not given: the volumes of water and ether, the amount of hydrochloric acid and the benzoic acid yield. Source: L. Gattermann, Practical Methods of Organic Chemistry (1914 ed.), Reaction 25, pp. 303-304. Picture: our drawing.
Hagati
1 night plus a few hours

Amabwiriza

1

Shake with strong potash

Dissolve 18 g of potassium hydroxide in 12 g of water and let it cool. Put 20 g of benzaldehyde in a stoppered cylinder or other thick-walled vessel, add the cold potash and shake until a lasting emulsion forms.

Ibikoresho by'iyi ntambwe:

BenzaldehydeBenzaldehyde1 20 g
Idorokiside ya potasiyumuIdorokiside ya potasiyumu1 18 g
AmaziAmazi1 12 g

Ibikoresho bikenewe:

UmunzaniUmunzani
Igikoresho gipima ibitembaIgikoresho gipima ibitemba
Ibipfundikizo by'ikorogoIbipfundikizo by'ikorogo
2

Stand overnight

Close the vessel with a cork, not a glass stopper (a glass stopper can stick fast), and let it stand overnight. A crystalline paste of potassium benzoate separates.

Ibikoresho bikenewe:

Igikoresho gipima ibitembaIgikoresho gipima ibitemba
Ibipfundikizo by'ikorogoIbipfundikizo by'ikorogo
3

Extract with ether

Add water until the paste dissolves to a clear solution. Shake it out several times with ether to take up the benzyl alcohol, keeping the watery alkaline layer for the benzoic acid.

Ibikoresho by'iyi ntambwe:

AmaziAmazi1 amount not given
Dietili etereDietili etere1 amount not given

Ibikoresho bikenewe:

Igifuniko gitandukanyaIgifuniko gitandukanya
Igikombe cy'IkirahureIgikombe cy'Ikirahure
4

Distil the benzyl alcohol

Evaporate the ether and distil the residue. Benzyl alcohol passes over at 206 °C. Yield: about 8 g.

Ibikoresho bikenewe:

Ubwogero bw'AmaziUbwogero bw'Amazi
Icupa ry'ikirahure ryo kuyungururaIcupa ry'ikirahure ryo kuyungurura
Konderanseri ikonjeshwa n'amaziKonderanseri ikonjeshwa n'amazi
Igipima UbushyuheIgipima Ubushyuhe
Itara rya BunsenItara rya Bunsen
5

Precipitate the benzoic acid

Acidify the alkaline solution with hydrochloric acid; benzoic acid is thrown down. Filter it off.

Ibikoresho by'iyi ntambwe:

Asidi ya kloridiriAsidi ya kloridiri1 amount not given

Ibikoresho bikenewe:

Igikombe cy'IkirahureIgikombe cy'Ikirahure
Akayunguruzo k'Ikirahure Gafite UmugoziAkayunguruzo k'Ikirahure Gafite Umugozi
Urupapuro rwo KuyungururaUrupapuro rwo Kuyungurura

Ibikoresho

5

Ibikoresho bikenewe

12

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Benzyl alcohol

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