Hydrochloric Acid → Ethyl (3-chlorobenzoyl)acetate

HRID 1610550Notes

Reaction equation

HRID 1610550 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[CH:5]=1)=[O:3].C(O)C.[H-].[Na+].Cl.[C:17](=O)([O:21]CC)[O:18][CH2:19][CH3:20]>O>[Cl:10][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH2:1][C:17]([O:18][CH2:19][CH3:20])=[O:21])[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7766Diethyl CarbonateHCID 149331-(3-Chlorophenyl)ethanoneHCID 24758Sodium hydride

Product 1

HCID 2757831Ethyl (3-chlorobenzoyl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-chloroacetophenone (23.9 g, 154 mmol) in diethyl carbonate (150 ml) was added ethanol (0.3 ml), and sodium hydride (60% in oil, 12.4 g, 309 mmol) was added under ice-cooling. The mixture was stirred at room temperature for 2 hrs. To the reaction solution was added 6N hydrochloric acid to stop the reaction, and water (500 ml) was added. Then, the mixture was extracted with ethyl acetate (500 ml×2). The extract was washed successively with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-5:1) to give the objective substance (24.8 g, 71%).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. additionwas added
  4. extractionThen, the mixture was extracted with ethyl acetate (500 ml×2)
  5. washThe extract was washed successively with water and saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-5:1)
  9. customto give the objective substance (24.8 g, 71%)

Sources & evidence

ORD record
ord-3fbdeac16d944931abf81cac1d8359ef
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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