Chloroacetone → HCID 23298223, compound

HRID 1953842Notes

Reaction equation

HRID 1953842 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.Cl[CH2:17][C:18](=[O:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[K+]>[O:20]=[C:18]([CH3:19])[CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 15541113HCID 15541113, compound

Product 1

HCID 23298223HCID 23298223, compoundYield 116.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

The title B compound of Example 1, 4'-hydroxy-[1,1'-biphenyl]-2-carbonitrile (3.00 g, 15.4 mmol) was dissolved in acetone (8 mL) and chloroacetone (1.59 mL, 20.0 mmol), freshly ground potassium carbonate (2.12 g, 15.4 mmol) and potassium iodide (128 mg, 0.77 mmol) were added. The mixture was heated to 60° C. for 15 hours then partitioned between hydrochloric acid (1.0 M) and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic extracts dried over magnesium sulfate, filtered and the solvent removed to yield a tan solid (4.51 g). This solid was recrystalized from a mixture of toluene and hexane to yield a tan solid (3.34 g, 87%); m.p. 102-105° C.

Workup

  1. customthen partitioned between hydrochloric acid (1.0 M) and ethyl acetate
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic extracts dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-8015ee1d2b6b45d7bb71303fdf3647e9
Source dataset
uspto-grants-2000_09
Patent number
US06117885

Reaction notes

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