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

HRID 899032Notes

Reaction equation

HRID 899032 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 (CAS Registry Number 13402-96-5) (11.05 g, 0.038 mol) and thionyl chloride (50 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. The residue was dissolved in 60-80 petroleum-ether (200 ml) and the solution was distilled under reduced pressure to remove volatiles, leaving 2-(2,4-di-t-pentylphenoxy)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. dissolutionThe residue was dissolved in 60-80 petroleum-ether (200 ml)
  5. distillationthe solution was distilled under reduced pressure
  6. customto remove volatiles

Sources & evidence

ORD record
ord-d1c56eadb2d348fbba4b90c9f395e25f
Source dataset
uspto-grants-2008_04
Patent number
US07354701B2

Reaction notes

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