Water → 4,5-Dichloro-2-methoxybenzoic acid

HRID 588826Notes

Reaction equation

HRID 588826 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.C1C(=O)N([Cl:20])C(=O)C1.O>C(#N)C>[Cl:1][C:2]1[C:10]([Cl:20])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 936824-Chloro-o-anisic acid

Product 1

HCID 211803434,5-Dichloro-2-methoxybenzoic acidYield 549%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-2-methoxybenzoic acid (10 g, 53.6 mmol) and NCS (35 g, 19.2 mmol) in acetonitrile (200 mL) was stirred at room temperature for 48 h. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo to get the crude product (23.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df3241ce08654e9d843839114ba90f11
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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