Water → 2-Propenal, 3-chloro-2,3-bis(3,4-dimethoxyphenyl)-

HRID 1087286

Reaction equation

HRID 1087286 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)=O)=[CH:5][C:4]=1[O:22][CH3:23].CN(C)[CH:26]=[O:27].O(Cl)[Cl:30].O>O1CCCC1>[CH3:23][O:22][C:4]1[CH:5]=[C:6]([C:9](=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[Cl:30])[CH:26]=[O:27])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24646Chlorine monoxideHCID 2311111,2-Bis(3,4-dimethoxyphenyl)ethanone

Product 1

HCID 3582202-Propenal, 3-chloro-2,3-bis(3,4-dimethoxyphenyl)-Yield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Desoxyveratroin (2.5 g, 0.0079 moles) was dissolved in a solution of tetrahydrofuran (20 ml) and a preformed solution of dimethylformamide (12 ml) and phophorous oxychloride (7 ml) was added with stirring over a period of 20 minutes to form a reaction mixture. The reaction mixture was kept below 30° by ice bath cooling and stirred for 5 hrs. The resulting slurry was then poured into water (200 ml) and stirred for 18 hrs. The crude product (2.9 g, mp. 162°-166°) was recrystallized from methanol-benzene to yield 1.7 g (59%) of the title compound as yellow needles, mp. 183°-184°. IR(mull): 1665, 1589 cm-1 ; 1H-NMR (CDCl3): δ3.93 (s, 12H), 7.0 (m, 6H), 9.8 (s, 1H); mass spectrum: M+ 364 (100%).

Workup

  1. customto form a reaction mixture
  2. customThe reaction mixture was kept below 30° by ice bath
  3. temperaturecooling
  4. stirringstirred for 5 hrs
  5. stirringstirred for 18 hrs
  6. customThe crude product (2.9 g, mp. 162°-166°) was recrystallized from methanol-benzene

Sources & evidence

ORD record
ord-9760494b9e204d418de260cc79dba6f8
Source dataset
uspto-grants-1991_07
Patent number
US05034544

Linked notes

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