Thionyl Chloride → HCID 20745768, compound

HRID 2307935Notes

Reaction equation

HRID 2307935 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4](O)=[O:5].S(Cl)([Cl:17])=O>CN(C=O)C.C1C=CC=CC=1>[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4]([Cl:17])=[O:5]

Participants

5

Reactant 2

HCID 24386Thionyl Chloride2×HCID 38711363-methyl-3-(4-methylphenyl)butanoic acid

Product 1

HCID 20745768HCID 20745768, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

A solution containing 3-methyl-3-(4-methylphenyl)butyric acid (8.5 g, 44.2 mmol) and anhydrous DMF (5 drops) in anhydrous benzene (110 mL) was refluxed under nitrogen as thionyl chloride (8.1 mL, 110 mmol)was added dropwise under nitrogen. The solution was refluxed an additional 15 h after complete addition of thionyl chloride. The dark brownish reaction mixture was allowed to cool to room temperature and concentrated under vacuum. TLC analysis of the crude material showed complete disappearance of the starting material. Presence of DMF was evident from the proton NMR. The crude material, 3-methyl-3-(4-methylphenyl)butyric acid chloride (305) (about 10 g), thus obtained was used in the next step without further purification.

Workup

  1. additionwas added dropwise under nitrogen
  2. temperatureThe solution was refluxed an additional 15 h
  3. customThe dark brownish reaction mixture
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-24534b4b69a340cfa50104867f4a54e4
Source dataset
uspto-grants-2004_12
Patent number
US06833372B2

Reaction notes

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