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Potassium acrylate → Acryloyloxymethyl 4-acryloyloxybutyl carbonate

HRID 580795
Notes
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Reaction equation

HRID 580795 reaction equation
[C:1](=[O:15])([O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:14])[CH:12]=[CH2:13])[O:2][CH2:3]Cl.[C:16]([O-:20])(=[O:19])[CH:17]=[CH2:18].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:1](=[O:15])([O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:14])[CH:12]=[CH2:13])[O:2][CH2:3][O:20][C:16](=[O:19])[CH:17]=[CH2:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4429391Potassium acrylateHCID 54357452Chloromethyl 4-acryloyloxybutyl carbonate

Product 1

HCID 54145101Acryloyloxymethyl 4-acryloyloxybutyl carbonateYield 91.1%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Procedure

Chloromethyl 4-acryloyloxybutyl carbonate (1.183 g, 5.00 mmol) prepared as described in Example 8 is added to a suspension of freeze dried potassium acrylate (0.606 g, 5.50 mmol) and 18-crown-6 (0.066 g, 0.25 mmol) in dimethylformamide (50 ml) under a dry N2 atmosphere. After 5 days at 20° C. the solvent is removed under reduced pressure and the residue dissolved by adding dichloromethane (60 ml) and water (30 ml). After separating the phases the aqueous layer is extracted with dichloromethane (3×30 ml) and the combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml). The organic phase is dried (MgSO4) and the solvent removed under reduced pressure to give 1.24 g (91%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.82 (4H, m, CH2 --CH2), 4.23 (4H, m, 2×CH2 --O), 5.88 (2H, s, O--CH2 --O), 5.7-6.8 (6H, 2×CH=CH2).

Workup

  1. customAfter 5 days at 20° C. the solvent is removed under reduced pressure
  2. dissolutionthe residue dissolved
  3. additionby adding dichloromethane (60 ml) and water (30 ml)
  4. customAfter separating the phases the aqueous layer
  5. extractionis extracted with dichloromethane (3×30 ml)
  6. washthe combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  7. dry with materialThe organic phase is dried (MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-77fbf36e757c4803bb95a2bcc5bd85e6
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05919753

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes