Isopropyl iodide → Benzonitrile, 3-methoxy-4-(1-methylethoxy)-

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[CH:18](I)([CH3:20])[CH3:19]>CC(C)=O>[CH:18]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11])([CH3:20])[CH3:19]

Participants

Procedure

25 g 4-Hydroxy-3-methoxy-benzonitrile, 27.8 g potassium carbonate and 33.5 mL isopropyl iodide were placed in 250 mL acetone and heated to reflux where they were maintained for 22 h. After this time the mixture was cooled to ambient temperature and concentrated under reduced pressure. The crude product was partitioned between ethyl acetate and water and the aqueous phase was separated and extracted with additional ethyl acetate. The combined organic fractions were dried, filtered and the solvent was removed from the filtrate under reduced pressure to give the title compound which was used without further purification.