Hydrochloric Acid → HCID 11140186, compound

HRID 1427018Notes

Reaction equation

HRID 1427018 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.[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:27])[CH3:26])[CH:19]=[O:20].Cl>C(O)C.O.C(OCC)(=O)C>[CH2:7]([O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:27])[CH3:26])[CH:19]=[O:20])[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 1545352194283-73-5

Product 1

HCID 11140186HCID 11140186, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (1.83 g, 13.2 mmol) and benzyl chloride (1.55 mL, 13.5 mmol) were added to a suspension of 3-hydroxy-4-isopropoxybenzaldehyde described in Production Example 171 (1.84 g, 10.2 mmol) in ethanol (20 mL) under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 90° C. for 2 hours. The mixture was cooled to 0° C. and then 2 M hydrochloric acid, ethyl acetate, and water were added for partition. The organic layer was washed with a saturated saline solution, and the resultant was dried over anhydrous sodium sulfate, and then filtered. The solvent was evaporated, the resultant residue was dissolved in dichloromethane, and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=19:1-3:1). The target fraction was concentrated under vacuum to obtain the title compound (2.59 g, 94%).

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 materialthe resultant was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. dissolutionthe resultant residue was dissolved in dichloromethane
  9. customthe resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=19:1-3:1)
  10. concentrationThe target fraction was concentrated under vacuum

Sources & evidence

ORD record
ord-3a5929b97bc8480e915d9f4df9009a08
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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