Methyl thiocyanate → HCID 20077557, compound

Temperature

4 °C

A solution of 4-ethylphenol (2.44 g) in dichloromethane (10 ml), was added to a stirred, ice-cooled, solution of 1M boron trichloride in dichloromethane (24 ml) under argon, followed by methylthiocyanate (1.64 ml), and then anhydrous aluminium chloride (2.66 g). The mixture was stirred for 1 hour at 4° C., then heated at reflux (bath temperature 60° C.) for 4 hours and finally stirred for 16 hours at ambient temperature. The mixture was added cautiously to a stirred, ice-cooled, 4M sodium hydroxide solution and the resultant mixture heated at 70° C. for 30 minutes then cooled. The aqueous phase was separated, washed with dichloromethane (2×25 ml), then acidified to pH2 with 6M hydrochloric acid and extracted with ethyl acetate (3×75 ml). The combined organic extracts were washed with saturated brine (3×50 ml), dried (MgSO4) and the solvent removed in vacuo to give a brown solid. Purification by flash chromatography, eluting with 20% v/v ethyl acetate in hexane, followed by recrystallisation from hexane gave 2-cyano-4-ethylphenol (A) (2.56 g), m.p. 95°-98° C.;

1. temperaturecooled
2. temperatureheated
3. temperatureat reflux (bath temperature 60° C.) for 4 hours
4. stirringfinally stirred for 16 hours at ambient temperature
5. additionThe mixture was added cautiously to a stirred, ice-
6. temperaturecooled
7. temperaturethen cooled
8. customThe aqueous phase was separated
9. washwashed with dichloromethane (2×25 ml)
10. extractionextracted with ethyl acetate (3×75 ml)
11. washThe combined organic extracts were washed with saturated brine (3×50 ml)
12. dry with materialdried (MgSO4)
13. customthe solvent removed in vacuo
14. customto give a brown solid
15. customPurification by flash chromatography
16. washeluting with 20% v/v ethyl acetate in hexane
17. customfollowed by recrystallisation from hexane

ORD record

ord-bf3e41565fe74c51a768f95a184fa89e

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05410064