4-Methoxybenzoic Acid → 3-Chloro-p-anisic acid

HRID 710294Notes

Reaction equation

HRID 710294 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[Cl:12]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[Cl:12][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[O:2][CH3:1])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 74784-Methoxybenzoic AcidHCID 31398Chlorosuccinimide

Product 1

HCID 1699823-Chloro-p-anisic acidYield 75.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-methoxybenzoic acid (0.46 g; 3 mmol) and N-chlorosuccinimide (NCS) (0.36 g; 2.7 mmol) in trifluoroacetic acid (5 ml) was stirred for 3 h at ˜70° C. After removing solvent under reduced pressure the residue was treated with H2O (10 ml). The solid was filtered off and purified by FCC (SiO2; EtOAc) to give the title compound (0.38 g; 68%) as a colourless solid. 1H-NMR (CDCl3) 3.97 (s, 3H); 6.96 (d, 1H, J=8.7 Hz); 8.0 (dd, 1H, J=2; 8.7 Hz); 8.11 (d, 1H, J=2 Hz).

Workup

  1. customAfter removing solvent under reduced pressure the residue
  2. additionwas treated with H2O (10 ml)
  3. filtrationThe solid was filtered off
  4. custompurified by FCC (SiO2; EtOAc)

Sources & evidence

ORD record
ord-d109e3dcbf2d414096ee07a90b6d0d6d
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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