HCID 54195713, compound → HCID 19018131, compound

HRID 1728425Notes

Reaction equation

HRID 1728425 reaction equation
[C:1]1([CH2:7][CH:8]([OH:22])[C:9]([O:11][CH2:12][C:13](=[O:21])OC2C=CC=CC=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1>[C:1]1([CH2:7][CH:8]2[O:22][C:13](=[O:21])[CH2:12][O:11][C:9]2=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 54195713HCID 54195713, compound

Product 1

HCID 19018131HCID 19018131, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
250 °C

Procedure

Experiment 8. 2-oxo-2-phenoxyethyl 3-phenyllactate (240 mL of a 10% w/v solution in tetrahydrofuran at 10 mL/hr) and nitrogen (240 mL/min) were passed through a 23-mm I.D. quartz tube containing 4 mL of coarsely crushed quartz on top of 4 mL of Catalyst A heated to 250° C. Contact time and WWH were 0.98 s and 0.77 hr-1, respectively. The column effluent was rotovaped, phenol was removed by distillation under reduced pressure to give crude product. Two crystallizations from anhydrous isopropanol gave 7.53 g (36.5 mmol) of 3-phenylmethyl-1,4-dioxane-2,5-dione. mp 64°-65° C. 1H NMR (300 MHz, CDCl3): δ3.28 (dd, 1H, J=5.7 and 14.6 Hz), δ3.37 (dd, 1H, J=4.6 and 14.7 Hz), δ3.89 (d, 1H, J=16.8 Hz), d 4.60 (d, 1H, J=16.8 Hz), δ5.17 (dd, 1H, J=4.6 and 5.7 Hz), and δ7.2-7.4 (phenyl, 5H). 13C NMR (75 MHz, CDCl3): 38.2, 65.0, 76.9, 128.1, 129.2, 130.1, 134.1, 163.4, and 165.1. HRMS calcd for C11H10O4 =206.0579, found 206.0574.

Workup

  1. customphenol was removed by distillation under reduced pressure
  2. customto give crude product
  3. customTwo crystallizations from anhydrous isopropanol

Sources & evidence

ORD record
ord-8cf5bab56fe045a4897991027a6a082d
Source dataset
uspto-grants-1994_07
Patent number
US05326887

Reaction notes

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