Epichlorohydrin → HCID 21162606, compound

HRID 893987Notes

Reaction equation

HRID 893987 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[CH:7]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1.N1CCCCC1.[Cl:24][CH2:25][CH:26]1[O:28][CH2:27]1>>[Cl:24][CH2:25][CH:26]([OH:28])[CH2:27][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[CH:7]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 8082PiperidineHCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

Product 1

HCID 21162606HCID 21162606, compound

Procedure

A mixture of 4.7 g of ethyl 7-hydroxychromone-2-carboxylate and 20 ml of 1-chloro-2,3-epoxypropane is heated at an external temperature of 100° C. for 8 hours in the presence of 0.2 ml of piperidine. The mixture is evaporated under reduced pressure and the residue is taken up with 15 ml of ethyl acetate. After filtration, the solution is evaporated under reduced pressure, the residue is taken up with 30 ml of chloroform and 10 ml of N hydrochloric acid, concentrated and stirred for one hour. The organic layer is washed with water, dried on anhydrous sodium sulfate and evaporated. The residue, crystallized from ethanol, gives 4 g of ethyl 7-(3-chloro-2-hydroxypropoxy)chromone-2-carboxylate. An amount of 1.65 g of the product thus obtained is dissolved in 40 mg of methylene chloride and to the solution thus obtained there is added 0.2 g of hexadecyltributylphosphonium bromide. To the organic solution there is added a solution of CH3SNa in 20 ml of water. The mixture is stirred for two hours at the room temperature, the aqueous layer is separated and acidified with N hydrochloric acid. The precipitate which forms, consisting of 7-(2-hydroxy-3-methylthiopropoxy)chromone2-carboxylic acid, is filtered and dried; m.p. 200°-202° C.

Workup

  1. customThe mixture is evaporated under reduced pressure
  2. filtrationAfter filtration
  3. customthe solution is evaporated under reduced pressure
  4. concentrationconcentrated
  5. washThe organic layer is washed with water
  6. dry with materialdried on anhydrous sodium sulfate
  7. customevaporated
  8. customThe residue, crystallized from ethanol

Sources & evidence

ORD record
ord-281930d7daa0474897d548b88807f102
Source dataset
uspto-grants-1981_08
Patent number
US04282247

Reaction notes

Loading…