Diethyl Ether → Benzoic Acid

Temperature

210 °C

The reaction is performed using the following set-up and procedure: quinic acid (20 mmol) was first dissolved in sulfolane at room temperature in a 50 ml three neck flask fitted with a fractioning column connected to a collecting flask through a U-shaped tube. The temperature in the reaction mixture is indicated by an immersed thermometer and nitrogen is bubbled through the mixture using a perforated tube immersed in the solution. Formic acid is then added and the mixture is heated over a preheated oil bath to 200-220° C. for a sufficient period of time. After that, the procedure is repeated adding another aliquot of formic acid. The reaction can be monitored by 1H NMR taking aliquots from the reaction mixture. Eventually the conversion of quinic acid is complete. Benzoic acid is isolated from the reaction mixture by extraction with ethyl ether and isolated removing the solvent at reduced pressure to give the product in a yield of over 75%.

1. customfitted with a fractioning column
2. customconnected to a collecting flask through a U-shaped tube
3. customis bubbled through the mixture
4. additionFormic acid is then added
5. additionAfter that, the procedure is repeated adding another aliquot of formic acid
6. customThe reaction

ORD record

ord-1284ebe91fb3426aaa114f0fc72303b7

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273926B2