Potassium hydroxide methanol → HCID 67403735, compound

HRID 906126Notes

Reaction equation

HRID 906126 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[C:5]([CH3:13])[C:4]=1[O:14][CH3:15])#[N:2].[OH-].[K+].CO>>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:13])[C:4]=1[O:14][CH3:15])#[N:2]

Participants

3

Reactant 2

HCID 23689386Potassium hydroxide methanolHCID 67403951Benzoic acid, 4-cyano-3-methoxy-2-methyl-, methyl ester

Product 1

HCID 67403735HCID 67403735, compoundYield 62%

Procedure

Methyl 4-cyano-2-methyl-3-(methyloxy)benzoate (150 mg, 0.73 mmol) in a solution of 35% aqueous potassium hydroxide:methanol (1:3, 4 mL) was stirred at 60° C. for 1 hour. The mixture was cooled to room temperature, and the methanol was removed by rotary evaporation. Water (4 mL) was added to the mixture and the pH was adjusted to 2 using concentrated aqueous hydrochloric acid. The precipitate which formed was collected by filtration and was washed with water, then hexanes to afford 86 mg, 0.45 mmol (62%) of 4-cyano-2-methyl-3-(methyloxy)benzoic acid. 1H NMR (400 MHz, d6-DMSO): 7.72 (d, 1H), 7.60 (d, 1H), 3.90 (s, 3H), 2.40 (s, 3H). MS (EI) for C10H9NO3: 190 (M−H).

Workup

  1. customthe methanol was removed by rotary evaporation
  2. additionWater (4 mL) was added to the mixture
  3. customThe precipitate which formed
  4. filtrationwas collected by filtration
  5. washwas washed with water

Sources & evidence

ORD record
ord-b40ff632ba1a4c59857363f964499900
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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