Vanillin → E-8-(4-Acetoxy-3-methoxybenzylidene)-5,6,7,8-tetrahydro-4-methylquinoline

HRID 464322Notes

Reaction equation

HRID 464322 reaction equation
[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.O=[CH:13][C:14]1[CH:22]=[CH:21][C:19]([OH:20])=[C:16]([O:17][CH3:18])[CH:15]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>[Cl-].[Zn+2].[Cl-]>[C:23]([O:20][C:19]1[CH:21]=[CH:22][C:14](/[CH:13]=[C:7]2\[CH2:8][CH2:9][CH2:10][C:11]3[C:2]([CH3:1])=[CH:3][CH:4]=[N:5][C:6]\2=3)=[CH:15][C:16]=1[O:17][CH3:18])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7918Acetic AnhydrideHCID 1856675,6,7,8-Tetrahydro-4-methylquinoline

Product 1

HCID 10245630E-8-(4-Acetoxy-3-methoxybenzylidene)-5,6,7,8-tetrahydro-4-methylquinoline

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of 5,6,7,8-tetrahydro-4-methylquinoline (5.2 g), vanillin (5.37 g), zinc chloride (0.3 g) and acetic anhydride (50 ml) were refluxed under nitrogen for 16 hours. The solvent was removed by evaporation and the resulting residue was neutralised (Na2CO3) in the presence of ethyl acetate and was then extracted with ethyl acetate.

Workup

  1. temperaturewere refluxed under nitrogen for 16 hours
  2. customThe solvent was removed by evaporation
  3. extractionwas then extracted with ethyl acetate

Sources & evidence

ORD record
ord-4f49006b3a8c48e883695fcfd9e08f68
Source dataset
uspto-grants-1985_10
Patent number
US04547510

Reaction notes

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