Methanol → HCID 28879848, compound

HRID 253163Notes

Reaction equation

HRID 253163 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)#[N:2].S(Cl)(Cl)=O.[CH3:19]O>>[C:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][CH2:9][C:10]([O:12][CH3:19])=[O:11])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 108215343-(4-cyanophenoxy)propanoic Acid

Product 1

HCID 28879848HCID 28879848, compoundYield 79%

Procedure

A solution of 3.80 g (19.9 mmol) of 3-(4-cyanophenoxy)propanoic acid in 10 ml of methanol is cooled by an ice bath. 3 ml (40 mmol) of thionyl chloride are added drop by drop and then the reaction medium is agitated with solvent reflux for 2 hours. The reaction mixture is then concentrated under reduced pressure and the evaporation residue is purified by silica column chromatography eluting with the help of a dichloromethane/methanol mixture (99/1; v/v). The expected product is obtained in the form of a white solid with a yield of 79%.

Workup

  1. temperaturereflux for 2 hours
  2. concentrationThe reaction mixture is then concentrated under reduced pressure
  3. customthe evaporation residue is purified by silica column chromatography
  4. washeluting with the help of a dichloromethane/methanol mixture (99/1; v/v)

Sources & evidence

ORD record
ord-e07b5f85bb9342fbb34a13bb02cfdf27
Source dataset
uspto-grants-2011_01
Patent number
US07872021B2

Reaction notes

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