Morpholine, 4-chloro- → 4,5-Dichloro-2-methoxybenzoic acid

HRID 1872687Notes

Reaction equation

HRID 1872687 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.[Cl:13]N1CCOCC1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:10]([Cl:13])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 90067Morpholine, 4-chloro-HCID 936824-Chloro-o-anisic acid

Product 1

HCID 211803434,5-Dichloro-2-methoxybenzoic acidYield 16.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

To an ice cold solution of 4-chloro-2-methoxybenzoic acid (1.0 g, 5.36 mmol) in trifluoroacetic acid (7 ml) was added N-chloromorpholine (0.67 g, 5.5 mmol) dropwise, maintaining the internal temperature below 10° C. After stirring overnight at room temperature the trifluoroacetic acid was removed in vacuo and the residue partitioned between ethyl acethate and water. The organic layer was dried over magnesium sulfate, concentrated in vacuo and the residue recrystallised from methanol to afford the title compound as a white solid (200 mg).

Workup

  1. temperaturemaintaining the internal temperature below 10° C
  2. customwas removed in vacuo
  3. customthe residue partitioned between ethyl acethate and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue recrystallised from methanol

Sources & evidence

ORD record
ord-c5ff3b1a7fd742159e25e5bec5dd1b66
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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