Dichloromethane → (3-Methoxyphenoxy)acetyl chloride

HRID 537291Notes

Reaction equation

HRID 537291 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8](O)=[O:9].C(Cl)[Cl:15].C(Cl)(=O)C(Cl)=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([Cl:15])=[O:9]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 749692-(3-Methoxyphenoxy)acetic acid

Product 1

HCID 13612584(3-Methoxyphenoxy)acetyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 500 mL flask fitted with a stir-bar, addition funnel, and an Ar inlet was charged with 3-methoxyphenoxyacetic acid (20.0 g, 110 mmol), CH2Cl2 (120 mL), and DMF (0.2 mL). Oxalyl chloride (2M in CH2Cl2, 69 mL, 137 mmol) was added to the resultant solution over 45 min forming an orange solution. The mixture stirred overnight at rt. The solution was concentrated in vacuo to give 22.7 g of 47b as an orange oil (100%). HPLC analysis (15:10:75 H2O:A1:MeOH) showed a purity of 93% with a retention time of 3.9 min.

Workup

  1. customA 500 mL flask fitted with a stir-bar, addition funnel
  2. customforming an orange solution
  3. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-ffefdc7e48074c7a8af0fb02bf679686
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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