Benzyl Chloride → HCID 86730338, compound

HRID 1427035Notes

Reaction equation

HRID 1427035 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][CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][C:22]=1[OH:29])[CH3:16]>C(O)C.Cl.C(OCC)(=O)C.O>[CH2:7]([O:29][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:21]=1[O:20][CH2:19][CH2:18][O:17][CH2:15][CH3:16])[CH:25]=[O:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 86730337HCID 86730337, compound

Product 1

HCID 86730338HCID 86730338, compoundYield 72%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (11.3 g, 81.5 mmol) and benzyl chloride (9.5 mL, 82.6 mmol) were added to a solution of 4-(2-ethoxyethoxy)-3-hydroxybenzaldehyde described in Production Example 24-1 (13.2 g, 62.7 mmol) in ethanol (130 mL) under nitrogen atmosphere at room temperature. The liquid mixture was stirred under a thermal condition of 90° C. for 2 hours. The reaction liquid was cooled to 0° C. and then diluted with 2 M hydrochloric acid, ethyl acetate, and water. The organic layer was washed with a saturated saline solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration and the filtrate was concentrated under vacuum. The resultant residue was dissolved in dichloromethane and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1) to obtain the title compound (13.5 g, 72%).

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to 0° C.
  3. washThe organic layer was washed with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe drying agent was separated by filtration
  6. concentrationthe filtrate was concentrated under vacuum
  7. dissolutionThe resultant residue was dissolved in dichloromethane
  8. customthe resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1)

Sources & evidence

ORD record
ord-be7afd38090a40c6aa96e1965bea5463
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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