Water → 3-(Cyclopentyloxy)-4-methoxyphenylacetonitrile

HRID 232786Notes

Reaction equation

HRID 232786 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-b5f2a7d91a2d4c54b96bae73af1798bc
Source dataset
uspto-grants-1997_01
Patent number
US05591776

Reaction notes

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