Sulfuric Acid → Methyl 4-Chloro-2-(3-hydroxy-3-oxo-1-propenyl)-benzoate

HRID 1282403Notes

Reaction equation

HRID 1282403 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].S(=O)(=O)(O)O.[C:22]([OH:26])(=[O:25])[CH:23]=[CH2:24]>O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2]>[Cl:16][C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH:24]=[CH:23][C:22]([OH:26])=[O:25])[CH:15]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6581Acrylic AcidHCID 80001Methyl 4-chloroanthranilateHCID 23668193Sodium Nitrite

Product 1

HCID 66938416Methyl 4-Chloro-2-(3-hydroxy-3-oxo-1-propenyl)-benzoate

Reagents, catalysts & solvents 2

HCID 5486778Palladium acetylacetonateCatalystHCID 962WaterSolvent2×

Procedure

At 2° C., a solution of 5.96 g of sodium nitrite in 11.3 ml of water is added to a mixture of 14 g of methyl 2-amino-4-chlorobenzoate, 59 ml of water and 14.3 ml of concentrated sulfuric acid. The reaction mixture is subsequently stirred for 20 minutes and then added a little at a time to 6.9 g of acrylic acid, 57 mg of palladium acetylacetonate being added after the first portion. After 4 hours at 40° C., the precipitated solid is filtered off, giving, after washing and drying, 18.5 g of methyl 4-chloro-2-(3-hydroxy-3-oxo-1-propenyl)-benzoate.

Workup

  1. additionadded after the first portion
  2. waitAfter 4 hours at 40° C.
  3. filtrationthe precipitated solid is filtered off
  4. customgiving
  5. washafter washing
  6. customdrying

Sources & evidence

ORD record
ord-c0befb4d8892433da5e40913fc7af121
Source dataset
uspto-grants-2002_09
Patent number
US06455725B1

Reaction notes

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