Hydrochloric Acid → 1-(4-Ethoxyphenyl)cyclopropanecarbonitrile

HRID 986406Notes

Reaction equation

HRID 986406 reaction equation
[CH2:1]([Li])[CH2:2]CC.[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=1)[CH3:7].ClC(Cl)C.Cl>C1COCC1>[C:16]([C:15]1([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:6][CH3:7])=[CH:10][CH:11]=2)[CH2:2][CH2:1]1)#[N:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 5839052-(4-Ethoxyphenyl)acetonitrileHCID 178418339Butyllithium

Product 1

HCID 135372511-(4-Ethoxyphenyl)cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

1.6M n-Butyllithium (680 ml) is added over 5 min to a stirred solution of 4-ethoxyphenyl acetonitrile (56 g) in anhydrous THF (600 ml) at 25° C. under an atmosphere of nitrogen. After 1 h, a solution of 1.2 dichloroethane (111 g) in anhydrous THF (300 ml) is added dropwise over 2 h and the mixture stirred at 25° C. for 16 h. The mixture is then poured onto 3N HCl (1 l ), concentrated under reduced pressure, extracted with diethyl ether (x3), washed with water, dried over anhydrous sodium sulphate, the solvent removed under reduced pressure and the residue distilled to give the product, b.p. 116°-120° C., yield 40 g. nD 1.5320.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with diethyl ether (x3)
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe solvent removed under reduced pressure
  6. distillationthe residue distilled
  7. customto give the product, b.p. 116°-120° C., yield 40 g

Sources & evidence

ORD record
ord-a27941921a974a759477b10eaf5cb161
Source dataset
uspto-grants-1987_12
Patent number
US04713392

Reaction notes

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