4-Phenoxybutyric acid → 4-Phenoxybutyryl chloride

HRID 1613604Notes

Reaction equation

HRID 1613604 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:16])=O>CN(C)C=O>[O:1]([CH2:8][CH2:9][CH2:10][C:11]([Cl:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 227414-Phenoxybutyric acidHCID 24386Thionyl Chloride

Product 1

HCID 788194-Phenoxybutyryl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

252.3 g (1.40 mole) of 4-phenoxybutyric acid, 154 ml (2.1 mole) of thionyl chloride and a few drops of dimethylformamide are heated under reflux with exclusion of moisture. After evolution of gas has ceased (about 2 hours), the mixture is fractionated under water pump vacuum. The acid chloride distils at 149°-151° C.

Workup

  1. temperatureunder reflux with exclusion of moisture
  2. custom(about 2 hours)
  3. customThe acid chloride distils at 149°-151° C.

Sources & evidence

ORD record
ord-59f398bb339c4f6fa1a9f06550d65bed
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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