beta-Phenylisovaleric acid → 3-Methyl-3-phenylbutanoyl chloride

HRID 432404Notes

Reaction equation

HRID 432404 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4](O)=[O:5].C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4]([Cl:17])=[O:5]

Participants

5

Reactant 2

HCID 13890beta-Phenylisovaleric acidHCID 65578Oxalyl chloride

Product 1

HCID 128675683-Methyl-3-phenylbutanoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-methyl-3-phenylbutyric acid (0.508 g, 2.85 mmol) in dichloromethane (10 mL) at −78° C. was treated with oxalyl chloride (3.62, 28.5 mmol) and 1 drop of dimethylformamide. The reaction mixture was stirred at −78° C. for 10 min, and dry ice/acetone bath was removed to stir at room temperature over night. Solvent was removed under reduced pressure, and dried under high vacuum. The product was used directly for subsequent reaction without analysis.

Workup

  1. customdry ice/acetone bath was removed
  2. stirringto stir at room temperature over night
  3. customSolvent was removed under reduced pressure
  4. customdried under high vacuum
  5. customThe product was used directly for subsequent reaction without analysis

Sources & evidence

ORD record
ord-bdac56215186421aab9e9bceacd19068
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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