Acetic Acid → 2,3-Dihydroxybenzoic Acid

HRID 2413522Notes

Reaction equation

HRID 2413522 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C[O:12]S([O-])(=O)=O.CC1C=CC=C2C=1N=C1C(C=CC=C1)=[NH+]2.C(O)(=O)C.O.NN>O.[Ni]>[OH:4][C:3]1[C:5]([OH:12])=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 338Salicylic AcidHCID 24654Hydrazine hydrate (1:1)HCID 178503009HCID 178503009, compound

Product 1

HCID 192,3-Dihydroxybenzoic AcidYield 861.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 962WaterSolvent

Procedure

0.15 g of salicylic acid and 0.03 g of 9-methylphenazinium methylsulphate are placed into a reactor and dissolved in 100 ml of water acidified by acetic acid to the pH=3.0; then 3.0 ml of hydrazine hydrate and 0.5 g of Raney nickel are added thereto. Thereafter, the reaction mixture is maintained for 4 hours under vigorous stirring. Then nickel is filtered-off, the resulting mixture is evaporated to 10 ml and extracted with chloroform. After cooling the precipitated desired product is crystallized by a mixture of water and ethanol in the ratio of 1:1 to give 0.13 g of 2,3-dihydroxybenzoic acid (90% as calculated for the starting compound) having m.p. 203°-204° C. The composition, in %, is as follows:

Workup

  1. temperatureThereafter, the reaction mixture is maintained for 4 hours under vigorous stirring
  2. customthe resulting mixture is evaporated to 10 ml
  3. extractionextracted with chloroform
  4. temperatureAfter cooling the
  5. customprecipitated desired product
  6. customis crystallized by a mixture of water and ethanol in the ratio of 1:1

Sources & evidence

ORD record
ord-df3837131b4441188f4fcd65db072ab6
Source dataset
uspto-grants-1988_01
Patent number
US04718994

Reaction notes

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