Epichlorohydrin → HCID 21450254, compound

HRID 596681Notes

Reaction equation

HRID 596681 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)[CH:7]=[CH:8][C:9]=1[OH:10])[CH:2]=[CH2:3].[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl.OC1C=CC=CC=1C(CCC(O)=O)=O.[OH-].[Na+]>ClCCl>[CH2:1]([C:4]1[CH:5]=[C:6]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:18][CH:20]1[O:22][CH2:21]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 30160863-(2-Hydroxybenzoyl)propionic acidHCID 1355732836-(3-allyl-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 21450254HCID 21450254, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of finely ground 6-(3-allyl-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (50g, 0.22 mole), epichlorohydrin (200 g, 2.2 mole) and piperidine (2g) was heated on a steam bath for 90 minutes. Evaporation under reduced pressure gave a viscous oil which was dissolved in dichloromethane and stirred for 10 minutes with dilute sodium hydroxide (500 ml). The organic phase was washed with water, dried and evaporated to an oil which slowly solidified. Addition of ethanol-ether gave 6[3-allyl-4-(2,3-epoxypropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone (30g, 47%, m.p. 92.5°-95° C) which was recrystallised from aqueous ethanol to give the pure pyridazinone (m.p. 93.5°-95° C).

Workup

  1. temperaturewas heated on a steam bath for 90 minutes
  2. customEvaporation under reduced pressure
  3. customgave a viscous oil which
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated to an oil which
  7. additionAddition of ethanol-ether

Sources & evidence

ORD record
ord-a2da714099554429bb63ad349a11e8a3
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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