HCID 53884703, compound → HCID 19018138, compound

HRID 1728424Notes

Reaction equation

HRID 1728424 reaction equation
OC(CCCC)[C:3]([O:5][CH2:6][C:7](=[O:15])[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11]C=1)=[O:4]>O1CCCC1>[CH2:14]([CH:9]1[O:8][C:7](=[O:15])[CH2:6][O:5][C:3]1=[O:4])[CH2:13][CH2:12][CH3:11]

Participants

3

Reactant 1

HCID 53884703HCID 53884703, compound

Product 1

HCID 19018138HCID 19018138, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
300 °C

Procedure

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.

Workup

  1. custom0 28 hr
  2. customphenol was removed by distillation under reduced pressure
  3. customwas obtained by distillation (13.2 g, 98°-110° C./0.1 mm Hg)
  4. customCrystallization from 30 mL of dry isopropanol

Sources & evidence

ORD record
ord-1b629a3c29d348dcb8c59210e5c03235
Source dataset
uspto-grants-1994_07
Patent number
US05326887

Reaction notes

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