Hydrochloric Acid → 4-Octylanisole

Participants

Reaction Conditions

Reaction Steps

In an argon atmosphere, 0.4 mmol (61 mg) of p-methoxyphenylboronic acid, 0.3 mmol (57 mg) of 1-bromooctane, 0.45 mmol (95 mg) of potassium phosphate, 0.015 mmol (2.6 mg) of bis(N-methylimidazole-2-yl)methane, and 0.015 mmol (4.1 mg) of bis(1,5-cyclooctadiene)nickel were mixed with 1 ml of N,N-dimethylacetamide. The resulting mixture was heated to 80° C. and then held at the same temperature for 2 hours under stirring. After the reaction was completed, the reaction mixture was allowed to stand at room temperature. After 10 ml of 1 N hydrochloric acid was added to dissolve potassium phosphate, the reaction mixture was transferred to a separating funnel and extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride solution. The 4-octylanisole was obtained in a yield of 87% as shown in Table 1.

Provenance & Evidence