Hydrochloric Acid → HCID 14451001, compound

HRID 2254775Notes

Reaction equation

HRID 2254775 reaction equation
[C:1]([C:3]1[C:4]([O:16]C(=O)C)=[C:5]([O:12]C(=O)C)[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1)#[N:2].[OH-].[Na+].Cl>CO.[Cl-].[Na+]>[C:1]([C:3]1[C:4]([OH:16])=[C:5]([OH:12])[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21459148HCID 21459148, compound

Product 1

HCID 14451001HCID 14451001, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5234Sodium ChlorideSolvent

Procedure

0.33 g of 5'-cyano-3',4'-diacetoxyacetophenone dissolved in 3.3 ml of methanol is treated with 2.7 ml of 1.0N sodium hydroxide solution and the reaction mixture is stirred at 23° for 45 minutes. The mixture is subsequently acidified with 2N hydrochloric acid, diluted with 5 ml of saturated sodium chloride solution and extracted twice with 30 ml of ethyl acetate each time. The combined ethyl acetate phases are dried over sodium sulfate and evaporated. The residue is recrystallized from toluene/acetonitrile. There is obtained 5'-cyano-3',4'-dihydroxyacetophenone as brownish crystals which decompose which decompose above 215°.

Workup

  1. extractionextracted twice with 30 ml of ethyl acetate each time
  2. dry with materialThe combined ethyl acetate phases are dried over sodium sulfate
  3. customevaporated
  4. customThe residue is recrystallized from toluene/acetonitrile

Sources & evidence

ORD record
ord-52cda71528964f619a095dff1e3ef473
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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