Methacrylic Acid → 2-HYDROXY-3-PHENOXYPROPYL METHACRYLATE

HRID 1894865Notes

Reaction equation

HRID 1894865 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1.[C:12]([OH:17])(=[O:16])[C:13]([CH3:15])=[CH2:14].C(N(CC)CC)C>C(Cl)Cl>[C:12]([O:17][CH2:2][CH:3]([OH:1])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:16])[C:13]([CH3:15])=[CH2:14]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 31217Phenyl glycidyl ether

Product 1

HCID 860932-HYDROXY-3-PHENOXYPROPYL METHACRYLATEYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

In a two neck flask equipped with a condenser under nitrogen atmosphere were placed 15.017 g (0.1 mol) of 1,2-epoxy-3-phenoxypropane, 9.039 g (0.105 mol) of methacrylic acid, 1.35 g (0.013 mol) of triethylamine and 30 mg of BHT. The reaction mixture was stirred at 60° C. 1H NMR showed reaction completion at 24 hours. Reaction mixtures was dissolved in methylene chloride and extracted with saturated solution of sodium hydroxide (NaOH) 3×25 ml, diluted solution of acid chloride (HCl) 2×25 ml, 2×25 ml of saturated solution of sodium bicarbonate (NaHCO3) and finally with brine 1×25 ml. Organic layer was dried over sodium sulfate (Na2SO4), filtered and vacuum dried. 20.14 grams (yield: 85%) of low viscosity (η=0.0891 Pa*s) amber material was obtained.

Workup

  1. customIn a two neck flask equipped with a condenser under nitrogen atmosphere
  2. customreaction completion at 24 hours
  3. customReaction mixtures
  4. extractionextracted with saturated solution of sodium hydroxide (NaOH) 3×25 ml, diluted solution of acid chloride (HCl) 2×25 ml, 2×25 ml of saturated solution of sodium bicarbonate (NaHCO3) and finally with brine 1×25 ml
  5. dry with materialOrganic layer was dried over sodium sulfate (Na2SO4)
  6. filtrationfiltered
  7. customvacuum dried
  8. custom20.14 grams (yield: 85%) of low viscosity (η=0.0891 Pa*s) amber material was obtained

Sources & evidence

ORD record
ord-516c5d3694d742049171a5ead0e35e9d
Source dataset
uspto-grants-2013_08
Patent number
US08513326B2

Reaction notes

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