Tri-o-tolylphosphine → Ethyl 2,6-diethyl-4-methylphenylacetate

Participants

Reaction Steps

Ethyl 2,6-diethyl-4-methylphenylacetate was prepared by the general experimental method from 2,6-diethyl-4-methylphenylboronic acid (186 mg, 1.00 mmol). This involved using 5.75 mg [0.01 mmol] of Pd(dba)2 and 9.1 mg [0.03 mmol] of P(o-tolyl)3. After workup by column chromatography (hexane/ethyl acetate, 5:1), ethyl 2,6-diethyl-4-methylphenylacetate is obtained as a colourless liquid in a yield of 54% of theory. 1H NMR (400 MHz, CDCl3): δ=6.91 (s, 2H), 4.16 (q, J=7.2 Hz, 2H), 3.71 (s, 2H), 2.61-2.69 (m, 4H), 2.32 (s, 3H), 1.19-1.28 (m, 9H) ppm; 13C NMR (101 MHz, CDCl3): δ=171.9, 143.0, 136.7, 127.2, 127.1, 60.6, 34.0, 26.4, 21.1, 15.1, 14.2 ppm; MS (70 eV), m/z (%): 234 (37) [M+], 161 (100), 147 (33), 133 (40), 119 (13); IR (NaCl): ν=2966 (s), 1739 (s), 1458 (w), 1156 (m), 1032 (m) cm−1; elemental analysis: (theor): C=76.88, H=9.46, (exp): C=75.85, H=9.38.

Provenance & Evidence