Methacrylic Acid → HCID 57679346, compound
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[C:10](O)(=[O:14])[C:11]([CH3:13])=[CH2:12]>ClCCl>[CH3:12][CH:11]1[CH2:13][C:4]2[C:3]3[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=3[S:1][C:5]=2[C:10]1=[O:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 67.5 °C
Procedure
A solution of 66.9 g of benzo[b]thiophene (0.5 mol) and 46.3 g of methacrylic acid (0.537 mol) in 60 ml of dichloromethane was added dropwise starting at 70° C. within 20 minutes to 1000 g of super-PPA. The temperature was maintained at 65-70° C. during the addition. Methylene chloride was distilled off. After 2 h of reaction time, the reaction mixture was poured onto crushed ice and stirred until the polyphosphoric acid had completely dissolved. The aqueous phase was extracted with a dichloromethane/hexane solvent mixture (30 parts by volume/70 parts by volume). The combined organic phases were washed with a saturated aqueous solution of sodium hydrogen-carbonate and with water and dried over magnesium sulfate. After removing the solvents under reduced pressure, 79.8 g of a dark orange oil (71%) were obtained.
Workup
- customstarting at 70° C. within 20 minutes to 1000 g of super-PPA
- distillationMethylene chloride was distilled off
- customAfter 2 h of reaction time
- additionthe reaction mixture was poured
- customonto crushed ice
- dissolutionhad completely dissolved
- extractionThe aqueous phase was extracted with a dichloromethane/hexane solvent mixture (30 parts by volume/70 parts by volume)
- washThe combined organic phases were washed with a saturated aqueous solution of sodium hydrogen-carbonate and with water
- dry with materialdried over magnesium sulfate
- customAfter removing the solvents under reduced pressure
Sources & evidence
- ORD record
- ord-16c94412eb6b4092b1a23163ac4b1c18
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531672B2
Reaction notes
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