Benzenepentanoic acid → 5-phenylpentanoyl Chloride

HRID 45378

Reaction equation

HRID 45378 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.C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C)C=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([Cl:17])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 16757Benzenepentanoic acidHCID 65578Oxalyl chloride

Product 1

HCID 109654605-phenylpentanoyl ChlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-phenylpentanoic acid (0.14 g, 0.81 mmol) in anhydrous dichloromethane (5 mL) was added two drops of N,N-dimethylformamide, followed by the addition of oxalyl chloride (0.11 g, 0.89 mmol). The reaction was stirred at ambient temperature for 2 hours. The solvent was removed in vacuo to dryness to afford 5-phenylpentanoyl chloride (0.16 g, 0.81 mmol) as a yellow oil.

Workup

  1. customThe solvent was removed in vacuo to dryness

Sources & evidence

ORD record
ord-0c858472ac714e4480308f6ec29b3a64
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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