Methyl Methacrylate → HCID 86595365, compound

HRID 1246183Notes

Reaction equation

HRID 1246183 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])=[O:5])#[N:2].[CH:16]([CH:18]=[CH2:19])=O.COC(=O)C(C)=C>[Cl-].[Zn+2].[Cl-].O1CCOCC1>[C:1]([C:3](=[CH:19][CH:18]=[CH2:16])[C:4]([O:6][CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])=[O:5])#[N:2]

Participants

6

Reactant 3

HCID 6658Methyl MethacrylateHCID 7847AcroleinHCID 85756799HCID 85756799, compound

Product 1

HCID 86595365HCID 86595365, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

35.2 g of methacryloyloxypropyl cyanoacetate is mixed with 50 ml of dioxane. 13.5 g of zinc chloride is added during mixing. 13,25 g of acrolein are added dropwise over 10 minutes, taking care the reaction temperature not to exceed 20° C. The stirring is continued for a further 8 hours at room temperature yielding a clear yellow solution. 100 ml of methylmethacrylate are mixed in and then three consecutive extractions with 150 ml of 2N hydrochloric aced are performed. The organic layer is filtered and stripped under reduced pressure (0.7 mm Hg). The pot temperature is not to exceed 90° C. and a steady stream of air through the product is maintained during stripping. 25 g of methacryloyloxypropyl 2-cyanopenta-2,4-dienoate are obtained with nD20=1,5045. The IR spectrum (FIG. 3) confirms the chemical structure. The product possesses the same adhesive properties as described in Example 1.

Workup

  1. additionduring mixing
  2. customto exceed 20° C
  3. customyielding a clear yellow solution
  4. extractionthree consecutive extractions with 150 ml of 2N hydrochloric
  5. filtrationThe organic layer is filtered
  6. customto exceed 90° C.
  7. temperaturea steady stream of air through the product is maintained during stripping

Sources & evidence

ORD record
ord-bb7fe135875e4742b08849b5be116a57
Source dataset
uspto-grants-2006_10
Patent number
US07125942B2

Reaction notes

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