3-Chloropropionic acid → HCID 13851425, compound

HRID 979168Notes

Reaction equation

HRID 979168 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[C:5]([CH3:10])[CH:4]=1.Cl[CH2:12][CH2:13][C:14]([OH:16])=[O:15].[F-].[Cs+].[OH-].[Na+]>CC#N>[CH3:10][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[S:9][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 78993-Chloropropionic acidHCID 14798Sodium HydroxideHCID 25953Cesium fluorideHCID 27595964-Methoxy-2-methylthiophenol

Product 1

HCID 13851425HCID 13851425, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 16.1 g 4-methoxy-2-methylbenzenethiol, 20 g 3-chloropropionic acid and 31.5 g CsF in 200 ml CH3CN is refluxed 40 hours. The cooled reaction mixture is poured into 200 ml 1N NaOH, and washed with 500 ml ether. The aqueous phase is acidified with 12N HCl and extracted with three 100 ml portions of CH2Cl2. The combined extracts are washed to 100 ml brine, dried over Na2SO4, filtered and evaporated to dryness in vacuo to afford 3-[(2-methyl-4-methoxyphenyl)thio]propanoic acid.

Workup

  1. temperatureis refluxed 40 hours
  2. customThe cooled reaction mixture
  3. washwashed with 500 ml ether
  4. extractionextracted with three 100 ml portions of CH2Cl2
  5. washThe combined extracts are washed to 100 ml brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d28cad14a2f6448896430d5f1e076320
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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