Methacrylic Acid → HCID 59609188, compound

HRID 1894866Notes

Reaction equation

HRID 1894866 reaction equation
C[CH:2]1[O:4][CH:3]1[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][CH:8]=1.[C:14]([OH:19])(=[O:18])[C:15]([CH3:17])=[CH2:16].[CH2:20](N(CC)CC)C>C(Cl)Cl>[C:14]([O:19][CH2:2][CH:3]([OH:4])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH3:20])[CH:10]=[C:11]([CH3:13])[CH:12]=1)(=[O:18])[C:15]([CH3:17])=[CH2:16]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 12882728HCID 12882728, compound

Product 1

HCID 59609188HCID 59609188, compoundYield 472.5%

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 10.00 g (0.0561 mol) of 3,5-dimethylphenoxymethyl oxirane, 5.07 g (0.059 mol) of methacrylic acid, 0.90 g (0.009 mol) of triethylamine and 30 mg of BHT. The reaction mixture was stirred at 60° C. 1H NMR showed reaction completion at 36 hours. Reaction mixtures was dissolved in methylene chloride and extracted with saturate 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. 11.24 grams (yield: 75%) of a amber viscous oil were obtained.

Workup

  1. customIn a two neck flask equipped with a condenser under nitrogen atmosphere
  2. customreaction completion at 36 hours
  3. customReaction mixtures
  4. extractionextracted with saturate 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

Sources & evidence

ORD record
ord-bfcf5cf04cb240849db7efb5c0f4c54d
Source dataset
uspto-grants-2013_08
Patent number
US08513326B2

Reaction notes

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