Methyl Salicylate → HCID 59737373, compound

HRID 1907774Notes

Reaction equation

HRID 1907774 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[OH:14][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.CCOC(C)=O>[CH3:20][O:19][C:17]([C:16]1[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=1[O:14][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])=[O:18]

Participants

6

Reactant 3

HCID 4133Methyl SalicylateHCID 10796Cesium carbonateHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 59737373HCID 59737373, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4-Fluoro-3-nitrobenzoic acid (5.0 g, 27.0 mmol), methyl 2-hydroxybenzoate (4.11 g, 27.0 mmol) and Cs2CO3 (18.49 g, 56.7 mmol) were dissolved in acetonitrile (100 mL) and stirred at 80° C. for 3 h. The reaction mixture was diluted with AcOEt and washed with 1M HCl and water. The organic layer was separated, dried with Na2SO4, filtered and concentrated via rotary evaporation to afford the title compound 545 (7.55 g, 88%) as a light yellow foam.

Workup

  1. washwashed with 1M HCl and water
  2. customThe organic layer was separated
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-e4e7e0dfbbd24123b32d2aca2e7812e3
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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