Hydrochloric Acid → (2E)-1-(2,4-difluorophenyl)-2-hydroxyiminopropan-1-one

HRID 433023Notes

Reaction equation

HRID 433023 reaction equation
[CH3:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=[O:4].CC1CCCCC1.Cl.C([O:26][N:27]=O)CCCC>>[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])/[C:2](=[N:27]/[OH:26])/[CH3:1]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7962MethylcyclohexaneHCID 10026Pentyl nitriteHCID 1235862',4'-Difluoropropiophenone

Product 1

HCID 20609430(2E)-1-(2,4-difluorophenyl)-2-hydroxyiminopropan-1-oneYield 88.6%

Conditions

Temperature
0 °C

Procedure

To a solution of 170 g (1.00 mol) of 2,4-difluoropropiophenone in 200 g methylcyclohexane 37 g (1.01 mol) of gaseous hydrochloric acid is dosed over 3 hours at 0° C. Thereafter 120 g (1.04 mol) of pentylnitrite are added over a period 3 to 4 hours to the reaction mixture at +10° C. to +15° C. Following the end of the addition the batch is stirred for an hour at +10° C. to +15° C. during which time a suspension is formed. The reaction mixture is then cooled to 0° C. and stirred for a further hour. The product is isolated by filtration and the filter cake is washed with 75 g of methylcyclohexane at 0° C.: 176 g of (E)-1-(2,4-difluoro-phenyl)-propane-1,2-dione-2-oxime (m.p. 99-101° C.) are obtained in 88.6% yield.

Workup

  1. additionthe end of the addition the batch
  2. customis formed
  3. stirringstirred for a further hour
  4. customThe product is isolated by filtration
  5. washthe filter cake is washed with 75 g of methylcyclohexane at 0° C.

Sources & evidence

ORD record
ord-cac912218ac44e9fa42236da914b3ae6
Source dataset
uspto-grants-2003_12
Patent number
US06664422B1

Reaction notes

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