1,2-Butanediol → 2-(4'-Chloro-2'-difluoromethoxyphenyl)-2-methyl-4-ethyl-1,3-dioxolane

HRID 2165769Notes

Reaction equation

HRID 2165769 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH:12]([F:14])[F:13])[CH:3]=1.[CH2:15](O)[CH:16]([OH:19])[CH2:17][CH3:18]>>[F:14][CH:12]([F:13])[O:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[C:8]1([CH3:9])[O:19][CH:16]([CH2:17][CH3:18])[CH2:15][O:10]1

Participants

3

Reactant 2

HCID 114291,2-ButanediolHCID 23043291Ethanone, 1-[4-chloro-2-(difluoromethoxy)phenyl]-

Product 1

HCID 230432952-(4'-Chloro-2'-difluoromethoxyphenyl)-2-methyl-4-ethyl-1,3-dioxolane

Procedure

12.8 parts of 1-(4-chloro-2-difluoromethoxyphenyl)ethan-1-one and 10.4 parts of 1,2-butanediol are heated under reflux for 12 hours in 100 ml of abs. toluene in the presence of 0.2 part of p-toluenesulfonic acid as catalyst, while removing the water of reaction with a water separator. The reaction mixture is cooled to room temperature and then washed with 2×100 ml of water, dried over sodium sulfate and filtered. The solvent is removed by evaporation and the residual oil is purified by high-vacuum distillation; b.p. 78°-80° C./0.04 mbar.

Workup

  1. temperatureunder reflux for 12 hours in 100 ml of abs
  2. customtoluene in the presence of 0.2 part of p-toluenesulfonic acid as catalyst, while removing
  3. customthe water of reaction with a water separator
  4. washwashed with 2×100 ml of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed by evaporation
  8. distillationthe residual oil is purified by high-vacuum distillation

Sources & evidence

ORD record
ord-8b2298ed088046ee9d25773c84e802bd
Source dataset
uspto-grants-1990_07
Patent number
US04940806

Reaction notes

Loading…