Hydrochloric Acid → HCID 818573, compound

HRID 1427012Notes

Reaction equation

HRID 1427012 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]([O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=1[OH:26])[CH3:16].Cl>C(O)C.O.C(OCC)(=O)C>[CH2:7]([O:26][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:18]=1[O:17][CH2:15][CH3:16])[CH:22]=[O:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 756794-Ethoxy-3-hydroxybenzaldehyde

Product 1

HCID 818573HCID 818573, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (19.8 g, 143 mmol) and benzyl chloride (16.5 mL, 143 mmol) were added to a suspension of 4-ethoxy-3-hydroxybenzaldehyde described in Production Example 15-1 (20 g, 120 mmol) in ethanol (200 mL) under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 90° C. for 2.5 hours. The mixture was cooled to 0° C., and 2 M hydrochloric acid, ethyl acetate, and water were added for partition. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated and the resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-4:1-3:1). The target fraction was concentrated under vacuum to obtain the title compound (28.5 g, 92%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled to 0° C.
  3. customfor partition
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customthe resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-4:1-3:1)
  9. concentrationThe target fraction was concentrated under vacuum

Sources & evidence

ORD record
ord-7edf8e512cda418c9c9b47de2f6a62e6
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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