Glycidyl methacrylate → 3-[4-(Dimethoxymethyl)phenoxy]-2-hydroxypropyl 2-methyl-2-propenoate

HRID 728628Notes

Reaction equation

HRID 728628 reaction equation
[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:13]([O:18][CH2:19][CH:20]1[O:22][CH2:21]1)(=[O:17])[C:14]([CH3:16])=[CH2:15]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[C:13]([O:18][CH2:19][CH:20]([OH:22])[CH2:21][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH:3]([O:11][CH3:12])[O:2][CH3:1])=[CH:5][CH:6]=1)(=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

4

Reactant 2

HCID 7837Glycidyl methacrylateHCID 11052043Phenol, 4-(dimethoxymethyl)-

Product 1

HCID 197857503-[4-(Dimethoxymethyl)phenoxy]-2-hydroxypropyl 2-methyl-2-propenoate

Reagents, catalysts & solvents 1

HCID 159952Benzyltributylammonium chlorideCatalyst

Conditions

Temperature
80 °C

Procedure

In a 500 ml. 4-neck flask fitted with a mechanical stirrer, thermometer, condenser and a vented nitrogen bubbler were placed 84 g. 4-dimethoxymethyl phenol (0.5 mole), 71 g. glycidyl methacrylate (GMA) (0.5 mole), and 1.5 g. benzyl tributyl ammonium chloride (0.005 mole). The apparatus was flushed with air for 5 minutes and the solution was then heated to 80° C. for 5 hours. The progress of the reaction was followed from disappearance of the GMA. Gas chromatographic analysis of the reaction mixture indicated 95% reaction. The solution was cooled and dissolved in 250 ml. methylene chloride and washed three times with lN sodium hydroxide (100 ml.) and then with water until the washings were neutral. The organic layer was dried over magnesium sulfate and the solvent was removed at reduced pressure using a Rotovap. The oily residue was dried under high vacuum for 30 minutes. The yield was 133 g. (86%) product. H-1 NMR showed signals typical of GMA except the signal for the protons that were attached to the epoxide carbon at 2.8 and 3.3 ppm showed up as doublets and a quintet respectively. The spectrum also showed signals for the 4-dimethoxymethylphenyl group at ppms 7.8-6.9 and 3.4.

Workup

  1. custom4-neck flask fitted with a mechanical stirrer
  2. customthermometer, condenser and a vented nitrogen bubbler were placed
  3. customThe apparatus was flushed with air for 5 minutes
  4. custom95% reaction
  5. temperatureThe solution was cooled
  6. dissolutiondissolved in 250 ml
  7. washmethylene chloride and washed three times with lN sodium hydroxide (100 ml.)
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. customthe solvent was removed at reduced pressure
  10. customThe oily residue was dried under high vacuum for 30 minutes

Sources & evidence

ORD record
ord-92ebe9236fc0418196646019736b3c4f
Source dataset
uspto-grants-1991_09
Patent number
US05049634

Reaction notes

Loading…