Reaktion #64765

Reaktionsgleichung

methyl-4-(hydroxymethyl)benzoate

sulfuric acid

water

→

title compound

Ausbeute 94.0%

4-Methoxycarbonylbenzenecarboxylic acid

Ausbeute 94.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe supernatant was decanted before the black tar-like residue
2. 2
   Extraktionwas extracted with acetone
3. 3
   Einengenconcentrated under vacuum
4. 4
   Sonstigeto leave a dark brown residue which
5. 5
   Sonstigewas triturated with cold water (4 liter)
6. 6
   SonstigeThe precipitate which formed
7. 7
   Sonstigewas collected
8. 8
   Waschenwashed three times with water (1 liter)
9. 9
   Sonstigedried

Vorschrift

Concentrated sulfuric acid (277.5 ml, 5.2 mol) was added dropwise over 1/2 hr to a stirred solution of chromium (VI) oxide (299.25 g, 2.99 mol) and water (925 ml) at 0°. The resulting solution was added dropwise over 1 hr to a stirred solution of methyl-4-(hydroxymethyl)benzoate (92.5 g, 0.564 mol) and acetone (4.6 1) at 0°. The reaction mixture was allowed to warm to room temperature and stirred overnight. The supernatant was decanted before the black tar-like residue was extracted with acetone. The decanted supernatant and acetone extracts were combined and concentrated under vacuum to leave a dark brown residue which was triturated with cold water (4 liter). The precipitate which formed was collected, washed three times with water (1 liter), and dried to give 94.6 g (94%) of the title compound as white crystals, m.p. 218°-221° C.

Quelle