Pyridine → 3,5-Dioxohexanoic acid

HRID 1862843Notes

Reaction equation

HRID 1862843 reaction equation
[CH:1]1[C:6]([CH:7]2[O:16][C:15]3[CH:14]=[C:13]([OH:17])[CH:12]=[C:11]([OH:18])[C:10]=3[CH2:9][CH:8]2[OH:19])=[CH:5][C:4]([OH:20])=[C:3]([OH:21])[CH:2]=1.[CH2-:22][C:23]([CH3:25])=[O:24].N1C=CC=CC=1.C(OC(=O)C)(=O)C>O>[CH3:14][C:13]([CH2:12][C:11]([CH2:10][C:15]([OH:24])=[O:16])=[O:18])=[O:17].[CH:1]1[C:6]([CH:7]2[O:16][C:15]3[CH:14]=[C:13]([OH:17])[CH:12]=[C:11]([OH:18])[C:10]=3[CH2:9][CH:8]2[OH:19])=[CH:5][C:4]([OH:20])=[C:3]([OH:21])[CH:2]=1.[CH2-:22][C:23]([CH3:25])=[O:24]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178516547HCID 178516547, compound

Product 2

HCID 54598443,5-Dioxohexanoic acidHCID 178516547HCID 178516547, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 g. of catechin acetonide were dissolved in 25 ml. of pyridine and 25 ml. of acetic anhydride added to the solution which was then left to react overnight at room temperature. The reaction mixture was subsequently poured with mechanical agitation into 500 ml. of water at 4°-5° C. The obtained precipitate was filtered and washed with water to neutrality. On crystallisation from a mixture of isopropanol and water, 5 g. of triacetate of catechin acetonide were obtained. The product melted at 120°-122° C. (Found: C, 63.12; H, 5.30; C24H24O9 requires: C, 63.16; H, 5.26).

Workup

  1. waitwas then left
  2. customto react overnight at room temperature
  3. additionThe reaction mixture was subsequently poured with mechanical agitation into 500 ml
  4. customat 4°-5° C
  5. filtrationThe obtained precipitate was filtered
  6. washwashed with water to neutrality
  7. customOn crystallisation
  8. additionfrom a mixture of isopropanol and water, 5 g

Sources & evidence

ORD record
ord-66fe0b93ad1a458a826ed2dd7dc1ab28
Source dataset
uspto-grants-1979_09
Patent number
US04166861

Reaction notes

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