Hydrochloric Acid → 2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetonitrile

Temperature

0 °C

Sodium cyanide (10.2 g) is dissolved in water (40 ml) and cooled to 0° C. A second solution comprising vanillin (15.5 g) and ethanol (30 ml) is added at 0° C. Now, concentrated hydrochloric acid (28.5 g 32%) is added to the mixture at 0 to +5° C. within 30 to 45 minutes and the dropping funnel is rinsed with water (10 ml). After confirming that the conversion has proceeded to a satisfactory level by HPLC, the mixture is worked up by extracting repeatedly with t-butyl methyl ether (3×50 ml). The collected organic phases are washed twice with 10% aqueous bisulfite (50 ml) and once with water (40 ml). Finally, the product solution is dried and the solvent is evaporated in vacuum to yield the crude product as a yellow oil, which crystallized on standing (mp 80-81° C.). If the already pure product needs further purification, it can be crystallized from ether/hexane (m.p82-83° C.).

1. washthe dropping funnel is rinsed with water (10 ml)
2. extractionby extracting repeatedly with t-butyl methyl ether (3×50 ml)
3. washThe collected organic phases are washed twice with 10% aqueous bisulfite (50 ml) and once with water (40 ml)
4. customFinally, the product solution is dried
5. customthe solvent is evaporated in vacuum

ORD record

ord-56f548f76e6a4413b8f5446f6b52e1b2

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07521579B2