4-Cyanophenol → HCID 18779131, compound

Temperature

127.5 °C

Sodium metal (1.10 g, 47.8 mmol) was dissolved in anhydrous methanol and 4-cyanophenol (5.70 g, 47.8 mmol) was added. The resultant solution was concentrated and dried under vacuum overnight. A mixture of this sodium salt and 4-cyanophenol (25 g, mp 110-113° C.) was heated to 125-130° C. and neat methyl N-(cyanomethyl)methanimidate (5.0 g, 51 mmol; Hosmane, R. S. et al, J. Org. Chem., 1212, 1984) was added dropwise over a period of 10 minutes under a slow stream of dry argon. The resultant mixture was stirred at 120° C. for 2 hours, cooled, and the reaction product partitioned between methylene chloride (500 mL) and aqueous sodium hydroxide (1 M, 500 mL). The aqueous layer was separated and extracted with methylene chloride (3×100 mL). The organic extracts were combined, washed with brine (100 mL), dried (K2CO3), and the solvent evaporated in vacuo. The residue was purified by chromatography (Silica gel, 3:7 acetone in CHCl3) to afford the title compound as a white powder.

1. concentrationThe resultant solution was concentrated
2. customdried under vacuum overnight
3. additionA mixture of this sodium salt and 4-cyanophenol (25 g, mp 110-113° C.)
4. temperaturecooled
5. customthe reaction product partitioned between methylene chloride (500 mL) and aqueous sodium hydroxide (1 M, 500 mL)
6. customThe aqueous layer was separated
7. extractionextracted with methylene chloride (3×100 mL)
8. washwashed with brine (100 mL)
9. dry with materialdried (K2CO3)
10. customthe solvent evaporated in vacuo
11. customThe residue was purified by chromatography (Silica gel, 3:7 acetone in CHCl3)

ORD record

ord-da178c4603ea40878156f34df244f205

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06080870