Tetrahydrofuran → alpha-n-Octyl-2,4-dichlorobenzyl cyanide

HRID 616388Notes

Reaction equation

HRID 616388 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#[N:6].O1CCCC1.[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O>[CH2:17]([CH:4]([C:5]#[N:6])[C:3]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=1[Cl:1])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 81401-BromooctaneHCID 805662,4-Dichlorophenylacetonitrile

Product 1

HCID 12343263alpha-n-Octyl-2,4-dichlorobenzyl cyanide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Sodium hydride (0.13 moles as a 50% dispersion in mineral oil) is washed with 100 mil. of dry n-hexane to remove the mineral oil, then blanketed with dry nitrogen and suspended in 250 ml. of freshly distilled tetrahydrofuran. To this sodium hydride suspension is added dropwise at room temperature, a solution of 2,4-dichlorobenzyl cyanide (25g., 0.13 mole) dissovled in 100 ml. of tetrahydrofuran. When the addition is completed the temperature is maintained at 30° C. for an additional 0.5 hours. A solution of n-octylbromide (27g., 0.14 mole) is then added dropwise and the resultant reaction mixture is stirred at 40 ° C. overnight under nitrogen. The reaction mixture is poured into 1 liter of water and extracted with (3 × 200 ml.) of ether. The combined ether extracts are washed, with water, dilute hydrochloric acid, saturated sodium, bicarbonate solution saturated sodium chloride solution,d and dried over magnesium sulfate. The solvent is evaporated to give 39.8g. (100%) of product.

Workup

  1. washSodium hydride (0.13 moles as a 50% dispersion in mineral oil) is washed with 100 mil
  2. customof dry n-hexane to remove the mineral oil
  3. additionTo this sodium hydride suspension is added dropwise at room temperature
  4. additionWhen the addition
  5. customthe resultant reaction mixture
  6. extractionextracted with (3 × 200 ml.) of ether
  7. washThe combined ether extracts are washed, with water, dilute hydrochloric acid, saturated sodium, bicarbonate solution saturated sodium chloride solution,d
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent is evaporated
  10. customto give 39.8g

Sources & evidence

ORD record
ord-fb05d81da5e042e09a022ac92783e399
Source dataset
uspto-grants-1978_02
Patent number
US04073921

Reaction notes

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