Tributylamine → HCID 53816732, compound

HRID 1156463Notes

Reaction equation

HRID 1156463 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](Cl)=O.[C:12](#[N:15])[CH:13]=C.C(N(CCCC)CCCC)CCC>CC1C=CC(C)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH:5]=[CH:13][C:12]#[N:15]

Participants

6

Reactant 3

HCID 7622TributylamineHCID 7855AcrylonitrileHCID 27585353,4-Dimethylbenzoyl chloride

Product 1

HCID 53816732HCID 53816732, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

0.448 g (2 millimols) of palladium acetate, 33.7 g (0.2 mol) of 3,4-dimethylbenzoyl chloride, 13.25 g (0.25 mol) of acrylonitrile and 37.06 g (0.2 mol) of tri-n-butylamine in 200 ml of p-xylene are stirred for 1.5 hours at 120° C. The mixture is then extracted by shaking with 200 ml of 2 N HCl, 200 ml of 2 N NaOH and 100 ml of water, after which it is dried for 15 minutes with 20 g of magnesium sulfate. The crude product is chromatographed on silica gel in methylene chloride, and is recrystallised from n-hexane. 10.0 g (32% of theory) of 3,4-dimethylcinnamonitrile are obtained as pale yellow crystals, melting point 93.9° C. Analysis for C11H11N: calculated C 84.04%, H 7.05%, N 8.91%; found C 83.65%, H 6.87%, N 9.03%.

Workup

  1. extractionThe mixture is then extracted
  2. dry with materialafter which it is dried for 15 minutes with 20 g of magnesium sulfate
  3. customThe crude product is chromatographed on silica gel in methylene chloride
  4. customis recrystallised from n-hexane

Sources & evidence

ORD record
ord-08190f128aaa40e3ad90b70f89604b6b
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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