Methacrylic Acid → HCID 18431813, compound

HRID 1278955Notes

Reaction equation

HRID 1278955 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]1([C:21]2[CH:25]=[CH:24][S:23][C:22]=2[CH3:26])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:27](O)(=[O:31])[C:28](C)=[CH2:29]>ClCCl>[CH3:26][C:22]1[S:23][C:24]2[CH2:29][CH2:28][C:27](=[O:31])[C:25]=2[C:21]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 4093Methacrylic Acid2×HCID 14812Phosphorus oxide (P4O10)2×HCID 27753082-methyl-3-phenylthiophene

Product 1

HCID 18431813HCID 18431813, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
100 °C

Procedure

In a 2 l 5 neck round bottled flask equipped with nitrogen inlet, 250 ml pressure equalized addition funnel, reflux condenser, thermometer, and mechanical stir was added 1 Kg polyphosphoric acid (Aldrich, 84%). The temperature was raised to 100° C., then 180 g-phosphorus pentoxide was added and the temperature was raised to 130° C. Stirring was continued until all the phosphorus pentoxide had dissolved then the flask and contents were cooled to 80° C. A solution containing 79.2 g (455 mmol) 3-phenyl-2-methylthiophene and 40.1 g (465 mmol) methacrylic acid (Aldrich) dissolved in 100 ml dichloromethane was added slowly. Stirring continued with refluxing dichloromethane for 7 h, during which time an additional 130.8 g (1.52M) methacrylic acid in 250 ml dichloromethane was added (in portions, every 1.5 h). The contents of the flask were poured on to ice, the organic layer was collected with 20% dichloromethane in hexane, washed with water, neutralized with a saturated solution of sodium bicarbonate, then again washed with water. The organic fraction was dried over magnesium sulfate, filtered, then the solvents were removed in vacuo. Yield: 71.4 g (65%) (89.32 g dark orange oil, 80% by GC: used in subsequent steps without further purification). The title compound was analysed by 1H-NMR spectroscopy.

Workup

  1. customequipped with nitrogen inlet
  2. additionaddition funnel
  3. temperaturereflux condenser
  4. temperaturethe temperature was raised to 130° C
  5. stirringStirring
  6. dissolutionhad dissolved
  7. temperaturethe flask and contents were cooled to 80° C
  8. additionwas added slowly
  9. stirringStirring
  10. customevery 1.5 h
  11. additionThe contents of the flask were poured on to ice
  12. customthe organic layer was collected with 20% dichloromethane in hexane
  13. washwashed with water
  14. washagain washed with water
  15. dry with materialThe organic fraction was dried over magnesium sulfate
  16. filtrationfiltered
  17. customthe solvents were removed in vacuo
  18. customYield: 71.4 g (65%) (89.32 g dark orange oil, 80% by GC: used in subsequent steps without further purification)

Sources & evidence

ORD record
ord-8cff45c450ae4706be7d5ad442951836
Source dataset
uspto-grants-2002_09
Patent number
US06444833B1

Reaction notes

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