2,3-Dimethylphenol → 2-(2,3-dimethylphenoxy)tetrahydro-2H-pyran

Participants

Reaction Steps

In a manner similar to Preparation 27 except use 2,3-Dimethylphenol (20 g, 0.164 mol), 1,2-dihyropyran (17.9 mL, 0.196 mol), p-toluenesulfonic acid (1.64 mmol), and triethylamine (1.80 mmol) to give 33.0 g (100%) of 2-(2,3-dimethylphenoxy)tetrahydro-2H-pyran as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.02 (t, J=7.8 Hz, 1H), 6.94 (d, J=8.1 Hz, 1H), 6.79 (d, J=7.4 Hz, 1H), 5.38 (t, J=3.2 Hz, 1H), 3.95-3.81 (m, 1H), 3.58 (dtd, J=11.2, 4.1, 1.3 Hz, 1H), 2.26 (s, 3H), 2.18 (s, 3H), 2.08-1.97 (m, 1H), 1.91-1.85 (m, 2H), 1.74-1.57 (m, 3H). 13C NMR (101 MHz, CDCl3) δ 155.00, 137.89, 125.92, 125.85, 123.15, 112.16, 96.46, 62.07, 30.75, 25.48, 20.23, 19.15, 11.90.

Provenance & Evidence