Allyl chloride → HCID 54210645, compound

HRID 1732145Notes

Reaction equation

HRID 1732145 reaction equation
[OH-].[Na+].[CH2:3]([C:6](=[CH:9][CH2:10][CH3:11])[C:7]#[N:8])[CH2:4][CH3:5].[CH2:12](Cl)[CH:13]=[CH2:14]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:9]([C:6]([CH2:12][CH2:13][CH3:14])([CH:3]=[CH:4][CH3:5])[C:7]#[N:8])[CH:10]=[CH2:11]

Participants

6

Reactant 3

HCID 7850Allyl chlorideHCID 14798Sodium HydroxideHCID 53943258HCID 53943258, compound

Product 1

HCID 54210645HCID 54210645, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 250 ml 4-neck flask equipped with stirrer, reflux cooler and dropping funnel, 20 g (0.5 moles) of solid sodium hydroxide, 80 ml of toluene and 5 g of tetrabutylammonium bromide are first introduced and heated to 80° C. To this 2-phase system, a mixture of 50 g (0.41 moles) of 2-propyl-2-pentenenitrile and 31.4 g (0.41 moles) of allyl chloride were added in doses within 30 minutes. The reaction mixture was maintained for 2 more hours at a temperature of 75° C. Further work proceeded as in Example 1. A yield of 24 g of desired product, corresponding to 29.4% of the theoretical, was obtained.

Workup

  1. customInto a 250 ml 4-neck flask equipped with stirrer
  2. temperaturereflux cooler
  3. additionwere added in doses within 30 minutes
  4. temperatureThe reaction mixture was maintained for 2 more hours at a temperature of 75° C

Sources & evidence

ORD record
ord-a697c163825d4c26a8852fe8b5846697
Source dataset
uspto-grants-1986_11
Patent number
US04625046

Reaction notes

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