Epichlorohydrin → HCID 54334007, compound

HRID 638034Notes

Reaction equation

HRID 638034 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:25])=[N:8][C:9]([CH3:24])=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:5])[CH3:2].[Na].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:25])=[N:8][C:9]([CH3:24])=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:27][CH:29]2[O:31][CH2:30]2)=[CH:14][CH:13]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 5360545SodiumHCID 135519086HCID 135519086, compound

Product 1

HCID 54334007HCID 54334007, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

9.0 g of the resulting 2,6-dimethyl-4-(4-hydroxyphenyl)-pyridine-3,5-dicarboxylic acid diethyl ester are dissolved in a solution prepared from 0.723 g of sodium metal and 80 ml of ethanol. This solution is slowly added drop-wise to a boiling solution of 11.9 ml of epichlorohydrin in 80 ml of ethanol; after cooling, the sodium chloride that is deposited is filtered off with suction and the filtrate is concentrated to dryness by evaporation. The residue is dissolved in ether and washed in succession with aqueous 1N sodium hydroxide solution, 1N hydrochloric acid, saturated aqueous potassium bicarbonate solution and finally with water. After distilling off the ether, the crude 2,6-dimethyl-4-[4-(2,3-epoxypropoxy)-phenyl]-pyridine-3,5-dicarboxylic acid diethyl ester is obtained in the form of a yellow oil.

Workup

  1. temperatureafter cooling
  2. filtrationthe sodium chloride that is deposited is filtered off with suction
  3. concentrationthe filtrate is concentrated to dryness by evaporation
  4. dissolutionThe residue is dissolved in ether
  5. washwashed in succession with aqueous 1N sodium hydroxide solution, 1N hydrochloric acid, saturated aqueous potassium bicarbonate solution and finally with water
  6. distillationAfter distilling off the ether

Sources & evidence

ORD record
ord-a04fa7e44198482d9634602d700ffb12
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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