Ethylene carbonate → HCID 14688769, compound

HRID 877314Notes

Reaction equation

HRID 877314 reaction equation
O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C(=O)([O-])[O-].[K+].[K+].C1(=O)[O:21][CH2:20][CH2:19][O:18]1>CN(C=O)C.C(OCC)(=O)C.O>[OH:18][CH2:19][CH2:20][O:21][C:4]1[C:3]([CH3:10])=[CH:2][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

7

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 14688769HCID 14688769, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-hydroxy-3-methyl-benzaldehyde (0.545 g, 4.00 mmol) in DMF (10 mL) was added potassium carbonate (1.10 g, 7.97 mmol). The reaction mixture was stirred at RT for 5 minutes and then a solution of ethylene carbonate (0.705 g, 8.00 mmol) in DMF (2 mL) was added. The resultant mixture was heated at 80° C. for 90 hours. The reaction mixture was allowed to cool and diluted with ethyl acetate and water. The organic phase was removed, washed with brine (×2), dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure to afford the title compound (0.677 g, 94%).

Workup

  1. temperatureto cool
  2. customThe organic phase was removed
  3. washwashed with brine (×2)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-b3cb41ada50842758830482ba0c5fb5d
Source dataset
uspto-grants-2015_03
Patent number
US08987299B2

Reaction notes

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