[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]
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).
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