1-chloro-4-prop-2-enoxybenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-chlorophenol (1.28 g, 10 mmoles), allyl methyl carbonate (1.40 g, 12 mmoles), palladium acetate (11 mg, 0.05 mmole) and triphenyl phosphine (40 mg, 0.15 mmole) is heated at 70° C. for 2.5 hours. After removal of volatiles, the residue is subjected to bulb-to-bulb distillation (110° C., 4 mm Hg) to give 1.64 g, 97 percent of allyl 4-chlorophenyl ether. After removal of volatiles the residue is subjected to bulb-to-bulb distillation (110° C., 4 mm Hg)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-chlorophenol (30 g, 233 mmol) in acetonitrile (100 ml) was added potassium carbonate (48.1 g, 349 mmol, 1.5 eq) and allyl bromide (36.28 g, 299.9 mmol, 1.3 eq) dropwise with stirring for 5 hours at 50° C. in an oil bath. The solids were filtered out and the liquid was concentrated under vacuum to afford 1-chloro-4-(prop-2-en-1-yloxy)benzene as yellow oil (34 g, 86%); 1H NMR (300 MHz, CDCl3): δ 7.20-7.25 (m, 2H), 6.81-6.86 (m, 2H), 5.96-6.09 (m, 1H), 5.27-5.44 (m, 2H), 4.49-4.51 (m, 2H). The solids were filtered out the liquid was concentrated under vacuum

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-chlorophenol (30 g, 233 mmol) in acetonitrile (100 ml) was added potassium carbonate (48.1 g, 349 mmol, 1.5 eq) and allyl bromide (36.28 g, 299.9 mmol, 1.3 eq) dropwise with stirring for 5 hours at 50° C. in an oil bath. The solids were filtered out and the liquid was concentrated under vacuum to afford 1-chloro-4-(prop-2-en-1-yloxy)benzene as yellow oil (34 g, 86%); 1H NMR (300 MHz, CDCl3): δ 7.20-7.25 (m, 2H), 6.81-6.86 (m, 2H), 5.96-6.09 (m, 1H), 5.27-5.44 (m, 2H), 4.49-4.51 (m, 2H). The solids were filtered out the liquid was concentrated under vacuum