Dichloromethane → HCID 86689279, compound

HRID 537286Notes

Reaction equation

HRID 537286 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][C:9](O)=[O:10])[CH3:2].C(Cl)[Cl:16].C(Cl)(=O)C(Cl)=O>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][C:9]([Cl:16])=[O:10])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 2361243-ethoxyphenoxyacetic acid

Product 1

HCID 86689279HCID 86689279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 250 mL flask fitted with a stir-bar, addition funnel, and an Ar inlet was charged with 3-ethoxyphenoxyacetic acid (13.0 g, 66.3 mmol) from above, CH2Cl2 (80 mL), and DMF (0.2 mL). To the resultant solution was added oxalyl chloride (2M in CH2Cl2, 41.4 mL, 82.8 mmol) over 30 min. The solution was stirred overnight then concentrated in vacuo to give 14.4 g of 47a as an oil/solid mix (100%). HPLC analysis (15:10:75 H2O:A1:MeOH) showed a purity of 95% with a retention time of 4.5 min.

Workup

  1. customA 250 mL flask fitted with a stir-bar, addition funnel
  2. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-f43963a056654679a50467dc0c7ab1cf
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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