Thionyl Chloride → Butanoyl chloride, 2-(3-pentadecylphenoxy)-

HRID 899030Notes

Reaction equation

HRID 899030 reaction equation
[CH2:1]([C:16]1[CH:17]=[C:18]([CH:26]=[CH:27][CH:28]=1)[O:19][CH:20]([CH2:24][CH3:25])[C:21](O)=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].S(Cl)([Cl:31])=O>ClCCl>[CH2:1]([C:16]1[CH:17]=[C:18]([CH:26]=[CH:27][CH:28]=1)[O:19][CH:20]([CH2:24][CH3:25])[C:21]([Cl:31])=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 85701Butanoic acid, 2-(3-pentadecylphenoxy)-

Product 1

HCID 112508Butanoyl chloride, 2-(3-pentadecylphenoxy)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Pentadecylphenoxy)butanoic acid (7.8 g, 0.02 mol) (CAS Registry Number 14230-52-5) and thionyl chloride (50 ml) were heated under reflux on a steam-bath for 1 h. The resulting yellow solution was allowed to cool before being distilled under reduced pressure to leave a yellow oil. The oil was dissolved in dichloromethane (50 ml) and the solution was distilled under reduced pressure to remove volatiles. The residual 2-(3-pentadecylphenoxy)butanoyl chloride was used without further purification.

Workup

  1. temperatureunder reflux on a steam-bath for 1 h
  2. temperatureto cool
  3. distillationbefore being distilled under reduced pressure
  4. customto leave a yellow oil
  5. distillationthe solution was distilled under reduced pressure
  6. customto remove volatiles
  7. customThe residual 2-(3-pentadecylphenoxy)butanoyl chloride was used without further purification

Sources & evidence

ORD record
ord-f98720d01107425aa34cf628bf1502ac
Source dataset
uspto-grants-2008_04
Patent number
US07354701B2

Reaction notes

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