Water → 3-(Cyclopentyloxy)-4-methoxyphenylacetonitrile

HRID 1859043Notes

Reaction equation

HRID 1859043 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 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. customthe layers were separated
  2. extractionThe methylene chloride solution was extracted several times with water
  3. customevaporated

Sources & evidence

ORD record
ord-230d30596b92453885f38fe1b080ee50
Source dataset
uspto-grants-2000_11
Patent number
US06153630

Reaction notes

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