Methacrylic Acid → HCID 19063423, compound

HRID 1900152Notes

Reaction equation

HRID 1900152 reaction equation
CC(C)([O-])C.[K+].[C:7]([OH:12])(=[O:11])[C:8]([CH3:10])=[CH2:9].[C:13](=[O:21])([O:17][CH:18](Cl)[CH3:19])[O:14][CH2:15][CH3:16].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[C:13](=[O:21])([O:17][CH:18]([O:11][C:7](=[O:12])[C:8]([CH3:10])=[CH2:9])[CH3:19])[O:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 4093Methacrylic AcidHCID 2855718-Crown-6HCID 162095Carbonic acid, 1-chloroethyl ethyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 19063423HCID 19063423, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert. butoxide (3.70 g, 0.033 mol) was added to a solution of methacrylic acid (2.84 g, 0.033 mol) in DMF (100 ml). Ethyl 1-chloroethyl carbonate (5.08 g, 0.033 mol) from Example 9 above was added to the resulting suspension. 18-crown-6 (0.61 g, 2.3 mmol) was then added and the reaction mixture was left with stirring at room temperature for 3 days. The reaction mixture was filtered and the solvent was removed under reduced pressure. The residue was dissolved in chloroform (100 ml) and washed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml). The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. Flash chromatography gave 2.50 g (38%) of the title product. (Adjusted for recovered starting material the yield was 75%).

Workup

  1. waitthe reaction mixture was left
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform (100 ml)
  5. washwashed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d5be19f84dcf4b6dbdda169ac5829a58
Source dataset
uspto-grants-1996_11
Patent number
US05574097

Reaction notes

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