Acetone → HCID 12732996, compound

HRID 1786520Notes

Reaction equation

HRID 1786520 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[OH:11])=[O:3].[CH3:12][C:13]([CH3:15])=O.N1CCCC1>CO>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]2[C:2](=[O:3])[CH2:1][C:13]([CH3:15])([CH3:12])[O:11][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 10515131-(4-Chloro-2-hydroxyphenyl)ethanone

Product 1

HCID 12732996HCID 12732996, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-chloro-2-hydroxyacetophenone (20 g, 0.1176 mol), acetone (13.3 mL, 0.1811 mol) and pyrrolidine (15 mL, 0.18 mol) in methanol (475 mL) was stirred at 25° C. overnight. The mixture was then concentrated to a red oil. Water was added and the solution was adjusted to pH 1 with concentrated hydrochloric acid. The product was extracted with diethylether. The organic layer was dried over magnesium sulfate and diethylether was evaporated under reduced pressure. The residue was dissolved in a small volume of methanol. The solution was treated with charcoal, filtered and water was added to the filtrate. The resulting precipitate was collected by filtration, washed with water and dried (79%). mp: 63-66° C., IR (KBr): υ: 3086 (C—H aromatic), 2976, 2931 (C—H aliphatic), 1693 (C=0) cm−1, Anal. (C11H11O2Cl) C, H.

Workup

  1. concentrationThe mixture was then concentrated to a red oil
  2. additionWater was added
  3. extractionThe product was extracted with diethylether
  4. dry with materialThe organic layer was dried over magnesium sulfate and diethylether
  5. customwas evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in a small volume of methanol
  7. additionThe solution was treated with charcoal
  8. filtrationfiltered
  9. additionwater was added to the filtrate
  10. filtrationThe resulting precipitate was collected by filtration
  11. washwashed with water
  12. customdried (79%)

Sources & evidence

ORD record
ord-4d56cf976bb44648b361f8bf4ea541af
Source dataset
uspto-grants-2009_03
Patent number
US07507761B2

Reaction notes

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