Hydrochloric Acid → HCID 86730362, compound

HRID 1427061Notes

Reaction equation

HRID 1427061 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.[F:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][C:21]=1[OH:28].Cl>C(O)C.O.C(OCC)(=O)C>[CH2:7]([O:28][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:20]=1[O:19][CH2:18][CH2:17][CH2:16][F:15])[CH:24]=[O:25])[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 86730361HCID 86730361, compound

Product 1

HCID 86730362HCID 86730362, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (3.87 g, 28.0 mmol) and benzyl chloride (3.2 mL, 27.8 mmol) were added to a suspension of 4-(3-fluoropropoxy)-3-hydroxybenzaldehyde described in Production Example 33-1 (4.62 g, 23.3 mmol) in ethanol (46 mL) under nitrogen atmosphere at mom temperature, and the mixture was stirred at 90° C. for 1.5 hours. The reaction mixture was cooled to 0° C., then 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 then filtered. The solvent was evaporated and the resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-3:2-1:1). The target fraction was concentrated under vacuum to obtain the title compound (6.14 g, 91%).

Workup

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

Sources & evidence

ORD record
ord-8cc4126d42d34a538aae85ac9cca7ff3
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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