2,2-Dimethyl-3-phenylpropanoic acid → 2,2-Dimethyl-3-phenylpropanoyl chloride

HRID 897687Notes

Reaction equation

HRID 897687 reaction equation
[CH3:1][C:2]([CH3:13])([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](O)=[O:4].C(Cl)(=O)C([Cl:17])=O>C(Cl)(Cl)Cl.CN(C)C=O>[CH3:1][C:2]([CH3:13])([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([Cl:17])=[O:4]

Participants

5

Reactant 2

HCID 218802,2-Dimethyl-3-phenylpropanoic acidHCID 65578Oxalyl chloride

Product 1

HCID 133072292,2-Dimethyl-3-phenylpropanoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,2-dimethyl-3-phenylpropanoic acid (0.856 g, 4.8 mmol) in chloroform (6 mL) at 0° C. was treated with oxalyl chloride (3.05 g, 24 mmol) and 1 drop of dimethylformamide. The reaction solution was stirred for 1 h at 0° C. The ice bath was removed and the reaction mixture stirred at room temperature over night. The solvent was removed under reduced pressure and dried under high vacuum to afford a quantitative amount of 2,2-dimethyl-3-phenylpropanoyl chloride. The oil was directly used in the following reaction.

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction mixture stirred at room temperature over night
  3. customThe solvent was removed under reduced pressure
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-12b4ab96b90640a6929caf207c51c6a2
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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