HCID 53884703, compound → HCID 19018138, compound

Participants

Reaction Conditions

Reaction Steps

Experiment 4. 2-Oxo-2-phenoxyethyl 2-hydroxycaproate (240 mL of a 10% w/v solution in tetrahydrofuran at 10 mL/hr) and nitrogen (300 mL/min) were passed through a 23-mm I.D. quartz tube containing 5 mL of coarsely crushed quartz on top of 15 mL of Catalyst A heated to 300° C. Contact time and WWH were 1.83 s and 0 28 hr-1 respectively. Conversion and selectivity, determined by integration of NMR spectra, were 100% and 80%, respectively. The column effluent was rotovaped, phenol was removed by distillation under reduced pressure, and a fraction which was predominantly product was obtained by distillation (13.2 g, 98°-110° C./0.1 mm Hg). Crystallization from 30 mL of dry isopropanol gave 8.28 g (48.1 mmol) 3-butyl-1, 4-dioxane-2,5-dione. mp 37°-39° C. 1H NMR (300 MHz, CDCl3): δ0.94 (t, 3H, J=7.2 Hz), δ1.4-1.6 (m, 4H), δ1.9-2.15 (m, 2H), δ4.89 (d, 1H, J=16.5 Hz), ca δ4.92 (m, 1H), and δ4.91 (d, 1H, J=16.5 Hz). 13C NMR: (75 MHz, CDCl3): 13.6, 22.0, 26.4, 30.5, 65.3, 75.6, 164.4, and 165.7. HRMS: calcd for C8H12O 4 =172. 0735, found 172. 0757.

Provenance & Evidence