smjp2



Place synthetic routes below

Step 1: Bromination of benzene Step 2: Formation of alcohol by making Grignard Reagent Step 3: Williamson ether synthesis Step 4: Alkyllation to add methyl groups Step 5: Bromination: N-bromosuccinimide is used to add bromium to benzylic position Step 6: Formation of nitrile by using cyanide ion via SN2 reaction Step 7: Bromination in order to make Grignard Reagent to make an alcohol Step 8: Williamson ether synthesis Step 9: Formation of aldehyde by adding POCl3 and DMF Step 10: Wittig reaction: preparation of ylide Step 11: Ylide reaction with aldehyde to form a final desired product

References:


 * 1) Wade, L.G. Organic Chemistry, p. 439-447, 754-763, 791, 835-638, 919.
 * 2)  Organic synthesis website < [] >
 * 3) Friedel-Crafts Alkylation of 1,4-Dimethoxybenzene 