Ethylene Glycol → 4-(1,3-Dioxolan-2-yl)phenyl 2-methylprop-2-enoate

HRID 327377Notes

Reaction equation

HRID 327377 reaction equation
[C:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][CH:8]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:15](O)[CH2:16][OH:17].C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[CH:11][CH:12]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 118924p-Formylphenyl methacrylateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 191082394-(1,3-Dioxolan-2-yl)phenyl 2-methylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 mL round bottom flask fitted with reflux condenser, Dean Stark trap and nitrogen line was charged with 30.0 g of 4-formylphenyl methacrylate, 19.0 g of ethylene glycol, 250 mL of toluene and a catalytic amount of p-toluenesulfonic acid monohydrate. The solution was heated at reflux for 1 day, during which time the water formed in the reaction was removed periodically from the Dean Stark trap. Toluene was added to make up for losses from the Dean Stark trap, and the solution was heated at reflux for an additional 15 hours. Thereafter the solution was cooled to room temperature, was washed with three 75 mL portions of saturated sodium bicarbonate solution, and the toluene extracts were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude acetal was chromatographed on silica gel (20:1 silica gel to compound weight ratio) with hexane/ethylacetate (4:1 volume ratio) to give purified acetal (18.8 g). 1H NMR (CDCL3) 7,5 (d, 2H), 7,1 (d, 2H), 6.3 (s, 1H), 5.78 (s, 1H), 5.7 (s, 1H), 4.15-3.85 (m, 4H), 2.02 (s, 3H); 13C NMR (CDC13) 165, 151, 135, 128, 127, 121, 103, 65, 18; IR (neat) 1735 cm-1 ester carbonyl. The spectral data are consistent with the postulated structure. The chromatographed acetal was used directly in the free radical polymerizations.

Workup

  1. customA 500 mL round bottom flask fitted
  2. temperaturewith reflux condenser
  3. temperatureThe solution was heated
  4. customformed in the reaction
  5. customwas removed periodically from the Dean Stark trap
  6. additionToluene was added
  7. temperaturethe solution was heated
  8. temperatureat reflux for an additional 15 hours
  9. washwas washed with three 75 mL portions of saturated sodium bicarbonate solution
  10. dry with materialthe toluene extracts were dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe crude acetal was chromatographed on silica gel (20:1 silica gel to compound weight ratio) with hexane/ethylacetate (4:1 volume ratio)
  14. customto give
  15. custompurified acetal (18.8 g)

Sources & evidence

ORD record
ord-3c9ebf6e9bd3431a90625790ec53d9a9
Source dataset
uspto-grants-1993_12
Patent number
US05273863

Reaction notes

Loading…