Ethyl Acetate → HCID 67007991, compound

HRID 1256937Notes

Reaction equation

HRID 1256937 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:12][O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=1.[C:24](OCC)(=[O:26])C>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][CH2:24][O:26][CH2:21][C:18]2[CH:19]=[CH:20][C:15]([C:14]([O:13][CH3:12])=[O:23])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 133974-Chlorobenzyl alcoholHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 67007991HCID 67007991, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chlorobenzyl alcohol (4.10 g) in N,N-dimethylformamide (110 ml), sodium hydride (60 to 72%, 952 mg) was added in an ice bath, and the mixed solution was stirred for 30 min. Then, to the resulting solution, 4-(bromomethyl)benzoic acid methyl ester (5.00 g) was added, and the mixed solution was stirred at room temperature for three hours. To the resulting solution, ethyl acetate was added. The resulting solution was washed with water and with a saturated saline solution, sequentially, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove the solvent. The resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate/n-hexane=5 to 9%) to give methyl 4-{[2-(4-chlorophenyl)ethoxy]methyl}benzoate (5.25 g).

Workup

  1. stirringthe mixed solution was stirred at room temperature for three hours
  2. washThe resulting solution was washed with water and with a saturated saline solution
  3. dry with materialsequentially, dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate/n-hexane=5 to 9%)

Sources & evidence

ORD record
ord-8775549d8f1f48c985d72d651a4e71f8
Source dataset
uspto-grants-2013_06
Patent number
US08461329B2

Reaction notes

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