Hydrochloric Acid → HCID 23316746, compound

HRID 1982476Notes

Reaction equation

HRID 1982476 reaction equation
[C:1]([CH:4]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)C(OCC)=O)(=[O:3])[CH3:2].Cl>C1COCC1>[N+:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:4][C:1](=[O:3])[CH3:2])=[CH:17][CH:16]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69974851HCID 69974851, compound

Product 1

HCID 23316746HCID 23316746, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 22.3 g (0.080 mol) of α-acetyl-4-nitrobenzenebutanoic acid, ethyl ester in 500 ml of THF was charged with 250 ml of 6N hydrochloric acid and refluxed overnight. The reaction mixture was cooled and evaporated to dryness under reduced pressure. The residue was diluted with water and extracted three times with diethyl ether. The organic extracts were separated, washed twice with 1N sodium hydroxide, three times with water and once with a saturated sodium chloride solution. The organic solution was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was distilled to remove the 4-chlorobutanol. The residue of this distillate was then further distilled through a 6 inch jacketed vigreaux column and fraction 2 therefrom afforded 6.681 g of 5-(4-nitrophenyl)-2-pentanone.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. customevaporated to dryness under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted three times with diethyl ether
  6. customThe organic extracts were separated
  7. washwashed twice with 1N sodium hydroxide, three times with water and once with a saturated sodium chloride solution
  8. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure
  10. distillationThe residue was distilled
  11. customto remove the 4-chlorobutanol
  12. distillationThe residue of this distillate was then further distilled through a 6 inch

Sources & evidence

ORD record
ord-bd4917ae4a784b2e9e1ebbd4d187f5c8
Source dataset
uspto-grants-1986_06
Patent number
US04596827

Reaction notes

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