Acetyl chloride → 3-(4-Nitro-phenoxy)-propionic acid methyl ester

HRID 2235827Notes

Reaction equation

HRID 2235827 reaction equation
[C:1](Cl)(C)=O.[N+:5]([C:8]1[CH:19]=[CH:18][C:11]([O:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1)([O-:7])=[O:6]>CO>[CH3:1][O:16][C:15](=[O:17])[CH2:14][CH2:13][O:12][C:11]1[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 3515353-(4-Nitrophenoxy)propionic acid

Product 1

HCID 156342353-(4-Nitro-phenoxy)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Neat AcCl (0.27 mL; 3.8 mmol) was added to a suspension of 3-(4-nitro-phenoxy)-propionic acid (1.591 g; 7.53 mmol) in dry MeOH (8.0 mL). A soln formed followed by a ppt. After sitting at 4° C. overnight, product was collected by filtration as a white microcrystalline solid (1.316 g; 78%). The mother liquor contained pure product by HPLC. LC-MS 226 ([M+H]+).

Workup

  1. customA soln formed
  2. filtrationproduct was collected by filtration as a white microcrystalline solid (1.316 g; 78%)

Sources & evidence

ORD record
ord-4b2daa1266e54c54954a23cbd703f109
Source dataset
uspto-grants-2010_05
Patent number
US07714022B2

Reaction notes

Loading…