Water → 3-(Cyclopentyloxy)-4-methoxyphenylacetonitrile

HRID 1377532Notes

Reaction equation

HRID 1377532 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-:17]#[N:18].[K+].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:10][C:17]#[N:18])[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 962WaterHCID 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 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-cyclopentyloxy-4-methoxybenzyl chloride (119 g, 0.49 mol), 120 ml of methylene chloride, KCN (70.7 g, 1.09 mol), benzyltriethylammonium chloride (35 g, 0. 015 mol) and water el20 ml) was stirred vigorously at room temperature for 48 hours when the reaction was complete by HPLC. 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 afford 3-cyclopentyloxy-4-methoxyphenylacetonitrile (109 g, 95%) of sufficient purity to be used in the subsequent transformation.

Workup

  1. customthe layers were separated
  2. extractionThe methylene chloride solution was extracted several times with water
  3. customevaporated

Sources & evidence

ORD record
ord-fae6f7deab4d49f1aa4664805a03df6a
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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