Toluene → HCID 66588777, compound

HRID 1784333Notes

Reaction equation

HRID 1784333 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]#[N:11])=[CH:4][CH:3]=1.[C-]#N.[Na+].[CH3:22][C:23]1[CH:30]=[CH:29][C:26](CCl)=[CH:25][CH:24]=1.[C:31]1(C)C=CC=CC=1>[OH-].[Na+]>[CH3:31][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:9]([C:26]2[CH:29]=[CH:30][C:23]([CH3:22])=[CH:24][CH:25]=2)([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:10]#[N:11])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 77224-Methylbenzyl chlorideHCID 8929Sodium CyanideHCID 86609628HCID 86609628, compound

Product 1

HCID 66588777HCID 66588777, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

Part b. Preparation of 4-Methyl-(α-(4-methylphenyl)-(α-[(4-methylphenyl)methyl]-benzenepropanenitrile: A flask containing 1.0 g (2 mmol) of sodium cyanide (95%) dissolved in 5 mL of 50% NaOH aqueous solution is charged with 0.3 g silica catalyst, followed by 4-methylbenzyl chloride (6.8 mmol) and 1 mL toluene. The flask is placed in an oil bath and heated at 40° C. with stirring for 48 h, after which 10 mL toluene is added. The organic layer is filtered and the filtrate evaporated to yield 4-methyl-α-(4-methylphenyl)-α-[(4-methylphenyl)methyl]-benzenepropanenitrile.

Workup

  1. additionis charged with 0.3 g silica catalyst
  2. customThe flask is placed in an oil bath
  3. filtrationThe organic layer is filtered
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-ddc6f8d40731455e8ef752e5ae687e4a
Source dataset
uspto-grants-2009_03
Patent number
US07504371B2

Reaction notes

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