Potassium Iodide → HCID 33753616, compound

HRID 964425Notes

Reaction equation

HRID 964425 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 33753616HCID 33753616, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.90 g (6.61 mmol) of 4'-hydroxyacetophenone, and 1.93 g (9.92 mmol) of ethyl 4-bromobutyrate in 1.80 mL of N,N-dimethylformamide is stirred for 48 hours, under dry conditions with 2.74 g (19.8 mmol) of potassium carbonate and 0.110 g (0.66 mmol) of potassium iodide. The reaction mixture is then evaporated under vacuum, and the residue partitioned between ether and water. The organic phase is separated, washed thrice with water, dried with magnesium sulfate, filtered, and evaporated under vacuum to give a brown solid. This is recrystallized from a warm ether-hexane mixture. The beige crystals are air dried, leaving 0.84 g (51%) of 4-(4-acetylphenoxy)butanoic acid, ethyl ester: m.p. 59°-61° C.; IR (KBr) 1740, 1670 cm-1 ; 1H-NMR (CDCl3) is consistent with the desired product; MS (FAB) m/e 251.1285 Δ=-0.2 mmμ (M+ +H). Analysis calculated. for C14 H18O4 : C, 67.18; H, 7.25; O, 25.57. Found: C, 67.16; H, 7.16; O, 25.68.

Workup

  1. customThe reaction mixture is then evaporated under vacuum
  2. customthe residue partitioned between ether and water
  3. customThe organic phase is separated
  4. washwashed thrice with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customto give a brown solid
  9. customThis is recrystallized from a warm ether-hexane mixture
  10. customdried

Sources & evidence

ORD record
ord-990025d2c7154cc9aac6a0f1a3ffb6d6
Source dataset
uspto-grants-1998_06
Patent number
US05767285

Reaction notes

Loading…