Acrylic Acid → HCID 19063430, compound

HRID 482197Notes

Reaction equation

HRID 482197 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 (Example li, 6.5 g, 0.052 mol) in DMF (150 ml) was added to the resulting suspension. 18crown-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-ef6fa73cccdb4c43a5ead21ec2572a93
Source dataset
uspto-grants-1998_08
Patent number
US05795562

Reaction notes

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