Acetic Acid → HCID 11587829, compound

HRID 1865121Notes

Reaction equation

HRID 1865121 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9](=[N:15]O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(O)(=O)C.O>C(O)C.[Zn]>[NH2:15][CH:9]([C:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 178472889HCID 178472889, compound

Product 1

HCID 11587829HCID 11587829, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 702EthanolSolvent2×

Conditions

Temperature
1 °C

Procedure

Step C″: Dissolve ethyl 3-(4-bromophenyl)-2-(hydroxyimino)-3-oxopropanoate (12.8 kg dry mass (15.75 kg wet), 42.65 mol, 1 eq, prepared in step B above) in ethanol (110 L) in a 400-L vessel at an internal temperature of 20° C. Cool the solution to an internal temperature of 1° C. over 20 min and add zinc dust (6.429 kg, 98.01 mol, 2.3 eq) portion-wise over 30 min at an internal temperature of 2 to 3° C. Prepare a solution of acetic acid (19.5 L), water (2.5 L), and ethanol (11.5 L) in a feeder. Add about 1 to 2% of the solution to the zinc suspension at 0° C. After 5 min, no exotherm is observed. Add another 1 to 2% of the solution. A rise of temperature could be observed. Add the rest of the solution, slowly in the beginning but continuously over 95 min at an internal temperature of −2 to 2° C. Cool the suspension to an internal temperature of −5° C. and stir for 15 min. to provide the title compound.

Workup

  1. additionAdd the rest of the solution
  2. waitslowly in the beginning but continuously over 95 min at an internal temperature of −2 to 2° C
  3. temperatureCool the suspension to an internal temperature of −5° C.

Sources & evidence

ORD record
ord-7a7708effacf481a86ce9915dd3807fe
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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