Methacrylic Acid → HCID 57679345, compound

HRID 492222Notes

Reaction equation

HRID 492222 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19](O)(=[O:23])[C:20]([CH3:22])=[CH2:21].CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>ClCCl>[CH3:21][CH:20]1[C:19](=[O:23])[C:9]2[S:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:10]=2[CH2:22]1

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 57679348HCID 57679348, compoundHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 57679345HCID 57679345, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 31.8 g of 2-phenyl-3-o-tolyl-thiophene (0.127 mol) and 13.3 ml of methacrylic acid (0.157 mol) was added within 30 minutes at about 80° C. to 500 ml of Eaton's reagent. On completion of the addition, the reaction mixture was stirred for a further 5 minutes and then gradually added to crushed ice. 300 ml of dichloromethane were added to dissolve the reaction product. The organic phase was removed, washed with a saturated aqueous solution of sodium hydrogencarbonate and dried over magnesium sulfate. After removing the solvent, 39 g of product (3) were obtained which, according to GC-MS, constituted a single, isomer and had a purity of 95%.

Workup

  1. additionOn completion of the addition
  2. additiongradually added
  3. customto crushed ice
  4. dissolutionto dissolve the reaction product
  5. customThe organic phase was removed
  6. washwashed with a saturated aqueous solution of sodium hydrogencarbonate
  7. dry with materialdried over magnesium sulfate
  8. customAfter removing the solvent

Sources & evidence

ORD record
ord-8ec0a7d2b29f40768c60569a6d6a62b8
Source dataset
uspto-grants-2009_05
Patent number
US07531672B2

Reaction notes

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