Thionyl Chloride → (2,4-Bis(1,1-dimethylpropyl)phenoxy)acetyl chloride

HRID 272259Notes

Reaction equation

HRID 272259 reaction equation
[C:1]([C:6]1[CH:16]=[C:15]([C:17]([CH2:20][CH3:21])([CH3:19])[CH3:18])[CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10](O)=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2].S(Cl)([Cl:24])=O>>[C:1]([C:6]1[CH:16]=[C:15]([C:17]([CH2:20][CH3:21])([CH3:19])[CH3:18])[CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10]([Cl:24])=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 83411(2,4-Bis(1,1-dimethylpropyl)phenoxy)acetic acid

Product 1

HCID 66612(2,4-Bis(1,1-dimethylpropyl)phenoxy)acetyl chloride

Procedure

2-(2,4-Di-t-pentylphenoxy)ethanoic acid (12.0 g, 0.041 mol) (CAS Registry Number 13402-96-5) and thionyl chloride (60 ml) were heated under reflux on a steam-bath for 1.5 h. The resulting yellow solution was allowed to cool before being distilled under reduced pressure to remove volatiles. The residue was dissolved in 60-80 petroleum-ether (200 ml) and the solution was distilled under reduced pressure to remove any remaining traces of volatiles, leaving 2-(2,4-di-t-pentyl-phenoxy)ethanoyl chloride as a red oil which was used without further purification.

Workup

  1. temperatureunder reflux on a steam-bath for 1.5 h
  2. temperatureto cool
  3. distillationbefore being distilled under reduced pressure
  4. customto remove volatiles
  5. dissolutionThe residue was dissolved in 60-80 petroleum-ether (200 ml)
  6. distillationthe solution was distilled under reduced pressure
  7. customto remove any remaining traces of volatiles

Sources & evidence

ORD record
ord-c9a630da5e8346fa98bc5ac0062931cb
Source dataset
uspto-grants-2008_11
Patent number
US07455959B2

Reaction notes

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