Water → HCID 54245544, compound

HRID 1862636Notes

Reaction equation

HRID 1862636 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[CH:4][C:3]=1[O:10][CH3:11].[C-:12]#[N:13].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][CH2:24]Cl)=[CH:18][CH:17]=1.O>CN(C)C=O.CO.[Co].C(OCC)(=O)C>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][CH2:24][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH2:6][CH2:12][NH2:13])=[CH:4][C:3]=2[O:10][CH3:11])=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 962Water2×HCID 8929Sodium CyanideHCID 62348Vanillyl alcoholHCID 53728250p-Chlorocinnamyl chloride

Product 1

HCID 54245544HCID 54245544, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 104730CobaltSolvent

Procedure

A mixture of 4-hydroxy-3-methoxybenzyl alcohol (76.1 g) and sodium cyanide (19.9 g) in dimethylformamide (250 ml) is stirred under an atmosphere of nitrogen for 3 hours at +120° C. The reaction mixture is cooled to +90° C. and 1-chloro-4-(3-chloro-propenyl)-benzene is added. The mixture is stirred at said temperature for 2 hours. After cooling it is poured into water (1000 ml) and extracted with ethyl acetate (2×500 ml). The organic layers are washed with brine (2×500 ml), dried (MgSO4) and evaporated. The residue is purified by flash column chromatography using silica gel and ethyl acetate/hexane (1:3). The product obtained is dissolved in methanol (400 ml) and hydrogenated over Raney-cobalt at +40° C. and 100 bar. Water (300 ml) and ethyl acetate (200 ml) are added. After filtration the reaction mixture is extracted with ethyl acetate (2×500 ml). The organic layers are washed with brine (2×200 ml), dried (K2CO3) and evaporated. 2-{4-[3-(4-Chloro-phenyl)-allyloxy]-3-methoxy-phenyl}-ethylamine is obtained.

Workup

  1. temperatureThe reaction mixture is cooled to +90° C.
  2. stirringThe mixture is stirred
  3. customfor 2 hours
  4. temperatureAfter cooling it
  5. extractionextracted with ethyl acetate (2×500 ml)
  6. washThe organic layers are washed with brine (2×500 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue is purified by flash column chromatography
  10. customThe product obtained
  11. filtrationAfter filtration the reaction mixture
  12. extractionis extracted with ethyl acetate (2×500 ml)
  13. washThe organic layers are washed with brine (2×200 ml)
  14. dry with materialdried (K2CO3)
  15. customevaporated

Sources & evidence

ORD record
ord-b2406d7c98184f4998c499402e971887
Source dataset
uspto-grants-2003_03
Patent number
US06538159B2

Reaction notes

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