Hydrochloric Acid → HCID 19261525, compound

HRID 549901Notes

Reaction equation

HRID 549901 reaction equation
[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.[H-].[Na+].[C:11]([C:14]1[CH:19]=[CH:18]C=[CH:16][CH:15]=1)(=[O:13])[CH3:12].Cl.[CH3:21][CH2:22][O:23][CH2:24][CH3:25]>C1C=CC=CC=1>[CH2:22]([O:23][C:24]1[CH:16]=[CH:15][C:14]([C:11]([CH2:12][C:1]([O:5][CH2:6][CH3:7])=[O:8])=[O:13])=[C:19]([CH3:18])[CH:25]=1)[C:21]1[CH:16]=[CH:15][CH:14]=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7410AcetophenoneHCID 7766Diethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 19261525HCID 19261525, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Diethyl carbonate (19.5 g, 165 mmol) was dissolved in ether (100 mL) and 50% suspension of sodium hydride in oil (8.0 g, 167 mmol) was carefully added. A solution of the above acetophenone (16.7 g, 69.3 mmol) in benzene (100 mL) was added and the mixture was refluxed for 5 h. After cooling, the mixture was poured on ice with concentrated hydrochloric acid (50 mL); the organic layer was separated, dried with anhydrous potassium carbonate and evaporated in vacuo. The residue was purified by column chromatography (silica gel Fluka 60, benzene/chloroform 1:1) affording ethyl 4-benzyloxy-2-methylbenzoylacetate.

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. dry with materialdried with anhydrous potassium carbonate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography (silica gel Fluka 60, benzene/chloroform 1:1)

Sources & evidence

ORD record
ord-9f20a4e918bb4ecb824296dee6f0ab21
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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