Hydrochloric Acid → HCID 19622754, compound

HRID 335352Notes

Reaction equation

HRID 335352 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].I[CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C=O)C>[OH:17][CH2:16][CH2:15][O:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH:6]=[O:7])=[CH:8][C:9]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8655SyringaldehydeHCID 11430Potassium CarbonateHCID 12225Iodoethanol

Product 1

HCID 19622754HCID 19622754, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Hydroxy-3,5-dimethoxybenzaldehyde (4.99 g, 27.4 mmol), 2-iodoethanol (9.43 g, 54.8 mmol), and potassium carbonate (7.56 g, 27.4 mmol) are added to 50 ml of DMF and left with stirring at 80° C. under a stream of nitrogen for 24 h. After cooling to RT, about 200 ml of water are added to the solution, which is acidified with 10% strength HCl and then extracted with chloroform. After drying with magnesium sulfate, the solvent is removed by distillation and the solid is isolated. For further purification, the solid is purified by column chromatography (flash: ethyl acetate/n-hexane (1:1)).

Workup

  1. waitleft
  2. temperatureAfter cooling to RT
  3. extractionextracted with chloroform
  4. dry with materialAfter drying with magnesium sulfate
  5. customthe solvent is removed by distillation
  6. customthe solid is isolated
  7. customFor further purification
  8. customthe solid is purified by column chromatography (flash: ethyl acetate/n-hexane (1:1))

Sources & evidence

ORD record
ord-26f0a0cf97b241199e2f36e3db4ac5b2
Source dataset
uspto-grants-2014_11
Patent number
US08883931B2

Reaction notes

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