Hydrochloric Acid → 3-(Benzyloxy)-4-(2-methoxyethoxy)benzaldehyde

HRID 1427029Notes

Reaction equation

HRID 1427029 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][CH2:25][CH2:26][O:27][CH3:28])[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][CH2:25][CH2:26][O:27][CH3:28])[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 426255193-Hydroxy-4-(2-methoxyethoxy)benzaldehyde

Product 1

HCID 867303313-(Benzyloxy)-4-(2-methoxyethoxy)benzaldehydeYield 93%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (11.8 g, 85.7 mmol) and benzyl chloride (10 mL, 86.9 mmol) were added to a liquid mixture of 3-hydroxy-4-(2-methoxyethoxy)benzaldehyde described in Production Example 20-1 (12.9 g, 65.9 mmol) in ethanol (130 mL) under nitrogen atmosphere at room temperature, and the mixture was heated under reflux 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, 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=9:1-1:1). The target fraction was concentrated under vacuum to obtain the title compound (17.6 g, 93%).

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=9:1-1:1)
  9. concentrationThe target fraction was concentrated under vacuum

Sources & evidence

ORD record
ord-3436fa1073f04318a56db6ead1875078
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

Loading…