Hydrochloric Acid → T5503425

HRID 433022Notes

Reaction equation

HRID 433022 reaction equation
[CH3:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].C([O:16][N:17]=O)(C)(C)C.O1CCCC1.Cl.C(=O)([O-])[O-].[Na+].[Na+].CC1CCCCC1>[Cl-].[Na+].O>[Cl:11][C:8]1[CH:7]=[CH:6][C:5]([C:3](=[O:4])/[C:2](=[N:17]/[OH:16])/[CH3:1])=[CH:10][CH:9]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7962MethylcyclohexaneHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 10906Tert-Butyl nitriteHCID 226974'-Chloropropiophenone

Product 1

HCID 9603109T5503425Yield 91.1%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 440 g (2.437 mol) of 4-chloropropiophenone and 335 g (2.925 mol) t-butylnitrite in 700 g of tetrahydrofurane 97.8 g (2.681 mol) of gaseous hydrochloric acid is dosed over 2 hours at +25° C. to +40° C. Following the end of the addition the batch is stirred for two hours at +15° C. to +30° C. The reaction mixture is neutralized by adding 630.5 g of 20% sodium carbonate solution at +25° C. Some brine and methylcyclohexane is added and the phases are separated. The product crystallizes from the organic phase when concentrated. The product is isolated by filtration and the filter cake is washed with 75 g of methylcyclohexane at 0° C.: 438.9 g of (E)-1-(4-chlorophenyl)-propan-1,2-dione-2-oxime (m.p. 115-115C.) are obtained in 91.1% yield.

Workup

  1. additionthe end of the addition the batch
  2. customthe phases are separated
  3. customThe product crystallizes from the organic phase when
  4. concentrationconcentrated
  5. customThe product is isolated by filtration
  6. washthe filter cake is washed with 75 g of methylcyclohexane at 0° C.

Sources & evidence

ORD record
ord-2517dc53bed0414cab40b57c973eccd8
Source dataset
uspto-grants-2003_12
Patent number
US06664422B1

Reaction notes

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