HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → (Z)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile

HRID 2902
Notes
Print preview

Reaction equation

HRID 2902 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[CH3:12])[CH:7]=O)([O-:3])=[O:2].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:25][C:26]#[N:27])[CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22].[OH-].[Na+]>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.O.ClCCl>[N+:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[C:25](/[C:17]2[CH:18]=[C:19]([O:23][CH3:24])[C:20]([O:21][CH3:22])=[C:15]([O:14][CH3:13])[CH:16]=2)\[C:26]#[N:27])[CH:9]=[CH:10][C:11]=1[CH3:12])([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 258873,4,5-TrimethoxyphenylacetonitrileHCID 17989983-Nitro-p-tolualdehyde

Product 1

HCID 10570105(Z)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrileYield 14.1%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chloride
Catalyst
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

5.0 g of 3-nitro-4-methylbenzaldehyde, 6.27 g of 3,4,5-trimethoxyphenylacetonitrile, 1.44 g of sodium hydroxide and 500 mg of trioctylmethylammonium chloride were dissolved in 25 ml of water and 500 ml of dichloromethane. The mixture was stirred vigorously for 3 hours at room temperature. The ice water was added to the mixture and the mixture was extracted with dichloromethane three times and dried over anhydrous sodium sulfate. The organic layer was concentrated and the residue was purified by silica gel column chromatography (dichloromethane) to give 1.5 g of the intended compound. The yield was 14.1%.

Workup

  1. extractionthe mixture was extracted with dichloromethane three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by silica gel column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-0522bf4210474a18b5909e43c5604b2d
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731353

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes