Toluene → HCID 13840075, compound

HRID 424033Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=NNS(C2C=CC(C)=CC=2)(=O)=O)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>O>[CH3:10][O:9][C:7]1[CH:6]=[C:5](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

39.4 g of N-[1-(3,5-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethylidene]-N′-tosylhydrazine (0.084 mol) prepared as in Example 30, 19.9 g of potassium ter-butoxide (0.177 mol) and 3.9 g of Triton X100® are introduced into a three-necked round-bottomed flask comprising 190 ml of toluene. The mixture is brought to reflux for 4 h, cooled to approximately 80° C. and 130 ml of water are introduced. Separation by settling is carried out and the aqueous phase is re-extracted with 90 ml of toluene. The toluene phases are washed with 50 ml of water and concentrated to result in 27.8 g of a brown solid, which is taken up in 30 ml of methanol and maintained for 1 h under agitation. The precipitate is filtered off, washed on the filter with methanol and dried. 16.6 g of (E)-3,5-dimethoxy-3′,4′-methylenedioxy-stilbene is recovered in the form of a brown solid, which exhibits a melting point of 96° C., i.e. a yield of 69% with respect to the starting hydrazone.

Workup

additionare introduced into a three-necked round-bottomed flask
temperatureto reflux for 4 h
customSeparation
extractionthe aqueous phase is re-extracted with 90 ml of toluene
washThe toluene phases are washed with 50 ml of water
concentrationconcentrated

Sources & evidence

ORD record: ord-90b5279007d143e29f994fb350721a9f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101804B2

Reaction notes

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