Dichloromethane → 3-(Cyclopentyloxy)-4-methoxyphenylacetonitrile

HRID 1419786Notes

Reaction equation

HRID 1419786 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:10]Cl)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)Cl.[C-:20]#[N:21].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:10][C:20]#[N:21])[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 109007664-(Chloromethyl)-2-(cyclopentyloxy)-1-methoxybenzene

Product 1

HCID 107282283-(Cyclopentyloxy)-4-methoxyphenylacetonitrileYield 96.2%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-cyclopentyloxy-4-methoxybenzyl chloride (119 grams, 0.49 mol), 120 milliliters of methylene chloride, KCN (70.7 grams, 1.09 mol), benzyltriethylammonium chloride (35 grams, 0.015 mol) and water (120 milliliters) was stirred vigorously at room temperature for 48 hours. The reaction mixture was diluted with. methylene chloride and the layers were separated. The methylene chloride solution was extracted several times with water and evaporated to yield 3-cyclopentyloxy-4-methoxyphenylacetonitrile (109 grams, 95%) for the subsequent transformation.

Workup

  1. additionThe reaction mixture was diluted with
  2. custommethylene chloride and the layers were separated
  3. extractionThe methylene chloride solution was extracted several times with water
  4. customevaporated

Sources & evidence

ORD record
ord-30df6b9f683642bca49ccc8263a0a1f8
Source dataset
uspto-grants-1999_03
Patent number
US05889014

Reaction notes

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