Hydrochloric Acid → HCID 21388143, compound

HRID 1833938Notes

Reaction equation

HRID 1833938 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]([CH3:11])=[CH:7][CH2:8][C:9]#[N:10].O.Cl.[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:5][C:6]([C:17]1[CH:18]=[CH:19][C:14]([CH3:20])=[CH:15][CH:16]=1)([CH3:11])[CH2:7][CH2:8][C:9]#[N:10]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 6383804-methylpent-3-enenitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21388143HCID 21388143, compoundYield 78.5%

Procedure

Aluminum chloride (100 g, 0.75 mol) was added slowly (30 minutes) to a solution of 4-methyl-3-pentenenitrile (61.7 g, 0.65 mol) in toluene (300 ml) while maintaining the temperature below 10° C. After stirring an additional 4.0 hours at a temperature below 10° C, the mixture was poured onto an ice, water mixture containing 100 ml of 10% hydrochloric acid. The organic layer was washed (10% Na2CO3 then H2O), concentrated and distilled to yield 94.8 g (78.5%) of 4-methyl-4-p-tolylpentanenitrile (3b) which was 91% the para isomer and 9% meta isomer (glc, 20M): bp 129° (1 mm); nD20 1.5145; δTMSCDCl 3 7.13 (s, 4), 2.28 (s, 3) 1.95 (s, 4); 1.28 (s,6).

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. washThe organic layer was washed (10% Na2CO3
  3. concentrationH2O), concentrated
  4. distillationdistilled

Sources & evidence

ORD record
ord-43d0e4457a5b4ff6bfb1b9b302324c5c
Source dataset
uspto-grants-1978_01
Patent number
US04067906

Reaction notes

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