Potassium Iodide → 4-(Benzyloxy)-2-[(5-methyl-5-cyanohexyl)oxy]-benzophenone

HRID 2228527Notes

Reaction equation

HRID 2228527 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[OH:18])=[O:3].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:27]([C:29]([CH3:36])([CH3:35])[CH2:30][CH2:31][CH2:32][CH2:33]Br)#[N:28]>CN(C)C=O.O>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:2][CH:1]=2)=[O:3])=[C:5]([O:18][CH2:33][CH2:32][CH2:31][CH2:30][C:29]([CH3:36])([C:27]#[N:28])[CH3:35])[CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 3092574'-Benzyloxy-2'-hydroxyacetophenoneHCID 46382156-Bromo-2,2-dimethylhexanenitrile

Product 1

HCID 235017844-(Benzyloxy)-2-[(5-methyl-5-cyanohexyl)oxy]-benzophenoneYield 111%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-benzyloxy-2-hydroxyacetophenone (2.45 g), potassium carbonate (3.25 g), potassium iodide (0.42 g), and 5-cyano-5-methyl-1-bromohexane (2.6 g) in dimethylformamide (40 mL) was heated at 90° C. for 22 hours under nitrogen. The slurry was cooled, poured into water (150 mL) and extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4), filtered, and concentrated under reduced pressure to an orange oil. This was purified by flash chromatography (ethyl acetate:hexane) to afford the product (2.4 g) as a clear oil. NMR(CDCl3): 1.37, s (6H); 1.64, m (4H); 1.89, m (2H); 2.58, s (3H); 4.03, t (3H); 5.09, s (2H); 6.50, s (1H); 6.58, d (1H); 7.37, m (5H); 7.81, d (1H). Mass Spec (GC-MS) m/z=365 (M).

Workup

  1. temperatureThe slurry was cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to an orange oil
  7. customThis was purified by flash chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-45c89c167de1440d9c685d4d26e4de99
Source dataset
uspto-grants-2002_07
Patent number
US06416733B1

Reaction notes

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