Methyl Methacrylate → HCID 58659609, compound

HRID 899494Notes

Reaction equation

HRID 899494 reaction equation
[CH3:1][CH:2]1[O:10][C:5]2([CH2:11][OH:12])[O:6][CH:7]([CH3:9])[CH2:8][N:4]2[CH2:3]1.[C:13](OC)(=[O:17])[C:14]([CH3:16])=[CH2:15]>>[CH3:1][CH:2]1[O:10][C:5]2([CH2:11][O:12][C:13](=[O:17])[C:14]([CH3:16])=[CH2:15])[O:6][CH:7]([CH3:9])[CH2:8][N:4]2[CH2:3]1

Participants

3

Reactant 2

HCID 6658Methyl MethacrylateHCID 68826255HCID 68826255, compound

Product 1

HCID 58659609HCID 58659609, compound

Conditions

Temperature
110 °C

Procedure

In an oven dried 300 mL round-bottom flask equipped with a reflux condenser were added 2,6-Dimethyl-tetrahydro-oxazolo[2,3-b]oxazol-7a-yl-methanol (789 g, 0.45 mol), methyl methacrylate (180.0 g, 1.80 mol), Prostab® 5415 (3.00 g, Ciba Specialty Chemicals, Basel, Switzerland) and titanium (iv) n-butoxide (6.00 g, 0.024 mol). The reaction content was heated to 110° C. for ˜8 hours GC analyses indicated ˜44% conversion. The reflux condenser was replaced with an oven dried distillation head and the distillate boiling between 60-70° C. collected. The distillation head was replaced with a reflux condenser and the reaction content heated to 120° C. for ˜4 hours, at the end of which GC analyses indicated the conversion to be ˜75%. Again the reflux condenser was replaced with a distillation head and the distillated boiling between 60-70° C. collected for ˜8 hours, at the end of which GC analyses indicated the conversion to be ˜90%. The reaction content was cooled to room temperature and the unreacted methyl methacrylate removed under vacuum and then the remaining reaction content vaccuum fractionally distilled affording four fractions:

Workup

  1. customIn an oven dried 300 mL round-bottom flask
  2. customequipped with a reflux condenser
  3. customThe reflux condenser was replaced with an oven
  4. customdried
  5. distillationdistillation head
  6. customboiling between 60-70° C.
  7. customcollected
  8. customThe distillation head was replaced with a reflux condenser
  9. temperaturethe reaction content heated to 120° C. for ˜4 hours, at the end of which GC analyses
  10. distillationthe distillated boiling between 60-70° C. collected for ˜8 hours, at the end of which GC analyses
  11. temperatureThe reaction content was cooled to room temperature
  12. customthe unreacted methyl methacrylate removed under vacuum
  13. customthe remaining reaction content vaccuum
  14. distillationfractionally distilled
  15. customaffording four fractions

Sources & evidence

ORD record
ord-a23e4b112eb54d7c951f974698d4d24a
Source dataset
uspto-grants-2008_04
Patent number
US07355050B2

Reaction notes

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