Thionyl Chloride → 2-(4-Chlorophenyl)-2-methylpropanoyl chloride

HRID 887209Notes

Reaction equation

HRID 887209 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9](O)=[O:10])=[CH:4][CH:3]=1.S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([Cl:16])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 804062-(4-Chlorophenyl)-2-methylpropionic acid

Product 1

HCID 135368632-(4-Chlorophenyl)-2-methylpropanoyl chlorideYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-Chlorophenyl)-2-methylpropanoic acid (3.85 g, 19.4 mmol) in toluene (5 mL) was treated with thionyl chloride (5.00 g, 3.1 mL) and heated at 80° C. for 2 hours. The cooled solution was concentrated under reduced pressure to provide a yellow oil containing a crystalline residue. The mixture was dissolved in hexane, filtered and the filtrate concentrated to provide the compound as a pale yellow oil (4.10 g, 98%).

Workup

  1. concentrationThe cooled solution was concentrated under reduced pressure
  2. customto provide a yellow oil
  3. additioncontaining a crystalline residue
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-ee2e314af5394f79834250f8f1a6546e
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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