Ethylene carbonate → 3-(2-Hydroxy-ethoxy)-5-methoxy-benzaldehyde

HRID 591858Notes

Reaction equation

HRID 591858 reaction equation
OC1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].[O:12]1[CH2:16][CH2:15][O:14][C:13]1=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:12][CH2:16][CH2:15][O:14][C:13]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 53145613-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 866620393-(2-Hydroxy-ethoxy)-5-methoxy-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-hydroxy-5-methoxy-benzaldehyde (12.0 g, 78.9 mmol) in anhydrous DMF (50 mL) was added [1,3]dioxolan-2-one (13.9 g, 157.0 mmol) and potassium carbonate (21.6 g, 157.0 mmol). The reaction mixture was then heated to 110° C. for 16 hours, then cooled to room temperature. Solid potassium carbonate was filtered and washed with ethyl acetate. The organic phase was collected and solvent was removed. The residue was purified by column chromatography (silica gel 230-400 mesh; eluting with 7:1 dichloromethane and ethyl acetate) to give 3-(2-hydroxy-ethoxy)-5-methoxy-benzaldehyde as a brown liquid. Yield: 10.0 g (65%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationSolid potassium carbonate was filtered
  3. washwashed with ethyl acetate
  4. customThe organic phase was collected
  5. customsolvent was removed
  6. customThe residue was purified by column chromatography (silica gel 230-400 mesh; eluting with 7:1 dichloromethane and ethyl acetate)

Sources & evidence

ORD record
ord-80a9783768c2446a9699767f2800eda5
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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