Water → 5-Cyano-3-methyl-2-benzofurancarboxylic acid

HRID 2091153Notes

Reaction equation

HRID 2091153 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13]C)=[O:12])=[C:8]([CH3:15])[C:7]=2[CH:16]=1)#[N:2].O1CCCC1.O.O.[OH-].[Li+]>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=[O:12])=[C:8]([CH3:15])[C:7]=2[CH:16]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66778156Methyl 5-cyano-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 218445275-Cyano-3-methyl-2-benzofurancarboxylic acidYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 5-cyano-3-methyl-1-benzofuran-2-carboxylate (4.20 g) synthesized above, tetrahydrofuran (80 mL), water (20 mL) and methanol (20 mL) was added lithium hydroxide monohydrate (1.64 g), and the mixture was stirred overnight at room temperature, and concentrated under reduced pressure. 1N Hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (3.58 g, 91%) as a pale-brown solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. addition1N Hydrochloric acid was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-48ba9fcb653c4d4bb66a503d03295bae
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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