Benzenepropanoic acid → Benzenepropanoyl chloride

HRID 537326Notes

Reaction equation

HRID 537326 reaction equation
[C:1]([OH:11])(=O)[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C=O)C.C(Cl)(C([Cl:21])=O)=O>C(Cl)Cl>[C:4]1([CH2:3][CH2:2][C:1]([Cl:21])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 107Benzenepropanoic acidHCID 6228DimethylformamideHCID 65578Oxalyl chloride

Product 1

HCID 64801Benzenepropanoyl chlorideYield 105.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 200 mL flask fitted with a stir-bar and septum with an Ar inlet was charged with hydrocinnamic acid (5.00 g, 33.3 mmol), DMF (0.1 mL), and CH2Cl2 (30 mL). To the resultant solution was added (COCl)2 (2M in CH2Cl2, 20.0 mL, 40.0 mmol) over 30 min. The mixture stirred overnight at rt, and then was concentrated in vacuo to give 5.9 g of 74 as a yellow oil (100%). HPLC analysis (15:10:75 H2O:A1:MeOH) showed a purity of 99% with a retention time of 5.3 min.

Workup

  1. customA 200 mL flask fitted with a stir-bar
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-984f97823af1496db38a80ed856f2816
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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