Methacrylic Acid → HCID 18329199, compound

HRID 2308127Notes

Reaction equation

HRID 2308127 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:7][O:8][C:9](=[O:22])/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20]O)=[CH:14][CH:13]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:7][O:8][C:9](/[CH:10]=[CH:11]/[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][O:5][C:1](=[O:6])[C:2]([CH3:4])=[CH2:3])=[CH:16][CH:17]=1)=[O:22]

Participants

6

Reactant 3

HCID 4093Methacrylic Acid2×HCID 10868Dicyclohexylcarbodiimide2×HCID 20716711HCID 20716711, compound

Product 1

HCID 18329199HCID 18329199, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

2.56 g (30 mmol) of methacrylic acid in 10 ml of THF were slowly added dropwise to a solution of 6 g (27 mmol) of (E)-3-[4-[2-hydroxyethoxy]phenyl]acrylic acid methyl ester, 5.85 g (28.3 mmol) of N,N′-dicyclohexylcarbodiimide (DCC) and 0.37 g (3 mmol) of 4-dimethylamino-pyridine in 80 ml of tetrahydrofuran (THF). The batch was stirred at room temperature overnight. In order to complete the reaction there were added firstly a further 1.46 g (7.1 mmol) of DCC and, after stirring for one hour, a further 0.5 g (5.9 mmol) of methacrylic acid. The batch was stirred for a further 24 hours, filtered and the filtrate was extracted 3 times each time with 200 ml of 5% acetic acid and 200 ml of water. The ether phase was dried over Na2SO4, evaporated and the residue was recrystallized from cyclohexane. Subsequently, the still slightly impure product was filtered over a thin silica gel layer (eluent:diethyl ether/hexane=1:1). This gave 8.3 g of 2-methylacrylic acid 2-[4-[(E)-2-(methoxycarbonyl)vinyl]phenoxy]ethyl ester as a white powder with a melting point of 81-82° C. and an absorption maximum of λmax. (in CH2Cl2)=306.5 nm (ε=23675 l/mmol cm).

Workup

  1. customthe reaction there
  2. stirringafter stirring for one hour
  3. stirringThe batch was stirred for a further 24 hours
  4. filtrationfiltered
  5. extractionthe filtrate was extracted 3 times each time with 200 ml of 5% acetic acid and 200 ml of water
  6. dry with materialThe ether phase was dried over Na2SO4
  7. customevaporated
  8. customthe residue was recrystallized from cyclohexane
  9. filtrationSubsequently, the still slightly impure product was filtered over a thin silica gel layer (eluent:diethyl ether/hexane=1:1)

Sources & evidence

ORD record
ord-e689d886648f432e993552035137afb5
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

Loading…