Chloroform → 2-(2,3-Dichloro-4-butyrylphenoxy)-2-methylpropionic acid

HRID 569120Notes

Reaction equation

HRID 569120 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][C:3]=1[OH:14].[OH-:15].[Na+].C(Cl)(Cl)Cl>CC(C)=O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][C:3]=1[O:14][C:6]([CH3:7])([CH3:5])[C:9]([OH:13])=[O:15]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 140998561-(2,3-Dichloro-4-hydroxyphenyl)butan-1-one

Product 1

HCID 201487022-(2,3-Dichloro-4-butyrylphenoxy)-2-methylpropionic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,3-dichloro-4-butyrylphenol (15 g, 0.064 mole), acetone (140 ml) and sodium hydroxide (14.5 g, 0.36 mole) was stirred and heated to reflux. Chloroform (12 g, 0.1 mole) was added to the mixture dropwise over a period of 15 minutes. Refluxing was continued for 3 hours and the acetone was evaporated in vacuo. The residue was treated with ice water containing hydrochloric acid. The product was extracted with ether. The ether extract was washed with water, then with brine and finally dried over MgSO4. The ether was evaporated in vacuo and the residue chromatographed on a column containing silica gel (320 g) and eluted with methylene chloride/tetrahydrofuran/acetic acid 50/1/1. The appropriate fractions were combined and evaporated in vacuo to give 10 g of 2-(2,3-dichloro-4-butyrylphenoxy)-2-methylpropionic acid which was identified by NMR and the purity confirmed by thin layer chromatography.

Workup

  1. temperatureheated to reflux
  2. temperatureRefluxing
  3. customthe acetone was evaporated in vacuo
  4. additionThe residue was treated with ice water
  5. additioncontaining hydrochloric acid
  6. extractionThe product was extracted with ether
  7. extractionThe ether extract
  8. washwas washed with water
  9. dry with materialwith brine and finally dried over MgSO4
  10. customThe ether was evaporated in vacuo
  11. customthe residue chromatographed on a column
  12. additioncontaining silica gel (320 g)
  13. washeluted with methylene chloride/tetrahydrofuran/acetic acid 50/1/1
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-3d71080d20504f11ade6b5e193b1e33b
Source dataset
uspto-grants-1988_03
Patent number
US04731381

Reaction notes

Loading…