Acrylic Acid → HCID 19063430, compound

HRID 1900157Notes

Reaction equation

HRID 1900157 reaction equation
CC(C)([O-])C.[K+].[C:7]([OH:11])(=[O:10])[CH:8]=[CH2:9].[C:12](=[O:21])([O:18][CH2:19]Cl)[O:13][CH2:14][CH2:15][CH2:16][CH3:17].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[C:12](=[O:21])([O:18][CH2:19][O:10][C:7](=[O:11])[CH:8]=[CH2:9])[O:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 6581Acrylic AcidHCID 2855718-Crown-6HCID 15256996Butyl chloromethyl carbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 19063430HCID 19063430, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium tert. butoxide (5.84 g, 0.052 mol) was added to a solution of acrylic acid (4.47 g, 0.045 mol) in DMF (220 ml). Butyl chloromethyl carbonate (6.5 g, 0.052 mol) in DMF (150 ml) was added to the resulting suspension. 18-crown-6 (0.6 g) was then added and the reaction mixture was left with stirring at room temperature for 2 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 4.57 g of the title product.

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-0e3620b4f8c44565a27c3be57a956513
Source dataset
uspto-grants-1996_11
Patent number
US05574097

Reaction notes

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