Dimethylformamide → 5-phenylpentanoyl Chloride

HRID 1934769Notes

Reaction equation

HRID 1934769 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O.CN(C)C=O>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([Cl:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 16757Benzenepentanoic acidHCID 24386Thionyl Chloride

Product 1

HCID 109654605-phenylpentanoyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 2.3 ml of methylene chloride was added 0.470 g of 5-phenylvaleric acid, to which were added at ambient temperature 0.287 ml of thionyl chloride and 0.020 ml of N,N-dimethylformamide. After a reaction at the same temperature as above for 4 hours, the reaction mixture was concentrated under reduced pressure, 5.0 ml of toluene was added and the resulting mixture was further concentrated under reduced pressure. Thus, 0.510 g of 5-phenylvaleric acid chloride was obtained as a light yellow oily product.

Workup

  1. customAfter a reaction at the same temperature as above for 4 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure, 5.0 ml of toluene
  3. additionwas added
  4. concentrationthe resulting mixture was further concentrated under reduced pressure

Sources & evidence

ORD record
ord-a4e92ca710fc4b16b021462ab381923d
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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