Water → 1-(4-Chloro-2-formyl-phenoxymethyl)-cyclopentanecarbonitrile

HRID 504531Notes

Reaction equation

HRID 504531 reaction equation
[C:1]([C:3]1([CH2:8][O:9]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[Cl:20][C:21]1[CH:22]=[CH:23][C:24](O)=[C:25]([CH:28]=1)[CH:26]=[O:27].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:9][CH2:8][C:3]2([C:1]#[N:2])[CH2:4][CH2:5][CH2:6][CH2:7]2)=[C:25]([CH:26]=[O:27])[CH:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 57750155HCID 57750155, compound

Product 1

HCID 577501211-(4-Chloro-2-formyl-phenoxymethyl)-cyclopentanecarbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the crude toluene-4-sulfonic acid 1-cyano-cyclopentylmethyl ester in DMF (70 mL) was added 5-chloro-2-hydroxy-benzaldehyde (12.48 g, 80 mmol) and K2CO3 (13.25 g, 96 mmol). After heated at 100° C. for 3 h, the reaction mixture was poured into water. The solution was diluted with EtOAc (200 mL), washed with water, dried and concentrated to give the title compound as a yellow oil (17.4 g). The oil was used for next step reaction directly without further purification.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-28bbaf0be2374418898938c32cfd87dd
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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