Toluene → HCID 66674281, compound

HRID 424032Notes

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]=CC3OCOC=3[CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C[C:35]([CH3:38])([O-:37])[CH3:36].[K+].[C:40]1(C)[CH:45]=CC=C[CH:41]=1>O>[CH3:10][O:9][C:7]1[CH:6]=[C:5](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:38][C:35]([O:37][CH:40]([CH3:45])[CH3:41])=[CH:36][CH:14]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

19 g of N-[1-(3,5-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethylidene]-N′-tosylhydrazine (0.39 mol) prepared as in Example 29. 9.3 g of potassium ter-butoxide (0.83 mol) and 1.9 g of Triton X100® are introduced into a three-necked round-bottomed flask comprising 100 ml of toluene. The mixture is brought to reflux for 3 h, cooled to approximately 90° C. and 70 ml of water are introduced. Separation by settling is carried out and the aqueous phase is re-extracted with 50 ml of toluene. The toluene phases are washed with 50 ml of water and concentrated to result in 12.3 g of a viscous product with a yellow color, which is taken up in 10 ml of methanol and maintained for 3 h under agitation. The precipitate is filtered off, washed on the filter with methanol and dried. 6.5 g of (E)-3,5-dimethoxy-4′-isopropyloxy-stilbene is recovered in the form of a white solid, which exhibits a melting point of 61° C., i.e. a yield of 55.6% with respect to the starting hydrazone.

Workup

temperatureto reflux for 3 h
customSeparation
extractionthe aqueous phase is re-extracted with 50 ml of toluene
washThe toluene phases are washed with 50 ml of water
concentrationconcentrated

Sources & evidence

ORD record: ord-9d5ea3be57a941179b0c1de510c14564
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101804B2

Reaction notes

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