Potassium Hydroxide → RP-101124

HRID 222872Notes

Reaction equation

HRID 222872 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15])[C:6]([O:8]C)=[O:7])#[N:2].[OH-].[K+]>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15])[C:6]([OH:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21956805Methyl 3-cyano-4-isopropoxybenzoate

Product 1

HCID 21956832RP-101124Yield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate (100 g, 463 mmol) in tetrahydrofuran (500 mL) was added 10% potassium hydroxide (500 mL). The resulting solution was allowed to warm to room temperature and maintained for 16 h, at which time it was concentrated to remove the tetrahydrofuran. The residue was diluted with water (500 mL) and washed with ether (2×500 mL). The aqueous layer was then acidified with 3 N HCl and stood for 2 h. The solids were collected by filtration and washed several times with water, then dissolved in methylene chloride (1 L). The mostly homogeneous mixture was filtered through Celite® and concentrated to a minimal volume of methylene chloride. Collection of the solids by filtration gave 82 g (87%) of 3-cyano-4-[(1-methylethyl)oxy]benzoic acid as a white solid.

Workup

  1. temperaturemaintained for 16 h, at which time it
  2. concentrationwas concentrated
  3. customto remove the tetrahydrofuran
  4. additionThe residue was diluted with water (500 mL)
  5. washwashed with ether (2×500 mL)
  6. filtrationThe solids were collected by filtration
  7. washwashed several times with water
  8. dissolutiondissolved in methylene chloride (1 L)
  9. filtrationThe mostly homogeneous mixture was filtered through Celite®
  10. concentrationconcentrated to a minimal volume of methylene chloride
  11. customCollection of the solids
  12. filtrationby filtration

Sources & evidence

ORD record
ord-4f822ebd297146e09a4250499f12b84b
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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