Allyl Alcohol → (3,4-Dichloro-phenoxy)-acetic acid allyl ester

HRID 23588

Reaction equation

HRID 23588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[O:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:14](O)[CH:15]=[CH2:16]>>[CH2:16]([O:8][C:7](=[O:9])[CH2:6][O:5][C:4]1[CH:10]=[CH:11][C:12]([Cl:13])=[C:2]([Cl:1])[CH:3]=1)[CH:15]=[CH2:14]

Participants

3

Reactant 2

HCID 7858Allyl AlcoholHCID 11495(3,4-Dichlorophenoxy)acetic acid

Product 1

HCID 69732160(3,4-Dichloro-phenoxy)-acetic acid allyl esterYield 96.8%

Procedure

To a solution of commercially available (3,4-dichloro-phenoxy)-acetic acid (2.65 g, 12.0 mmol) in allyl alcohol (12.0 cm3, 180 mmol) at ambient temperature under an atmosphere of dry nitrogen was added 4 drops concentrated sulfuric as a catalyst. The solution was stirred at ambient temperature for 20 hours and the volatile fractions removed in vacuo. The residue was dissolved in ethyl ether (50 cm3), washed with water (25 cm3), washed with saturated sodium bicarbonate (25 cm3), washed with brine (25 cm3), dried over magnesium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to afford the title compound as a colorless viscous oil (3.02 g, 96.8%) with positive ion ESI (M+H)+261.3.

Workup

  1. concentrationconcentrated sulfuric as a catalyst
  2. customthe volatile fractions removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl ether (50 cm3)
  4. washwashed with water (25 cm3)
  5. washwashed with saturated sodium bicarbonate (25 cm3)
  6. washwashed with brine (25 cm3)
  7. dry with materialdried over magnesium sulfate, vacuum
  8. filtrationfiltered
  9. customthe filtrate volatile fractions removed in vacuo

Sources & evidence

ORD record
ord-603affca2e4842b7b2bec7915cb213f2
Source dataset
uspto-grants-2005_02
Patent number
US06852713B2

Linked notes

Loading…