Potassium Hydroxide → HCID 66616530, compound

HRID 1889637Notes

Reaction equation

HRID 1889637 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:14]([O:16]C)=[O:15])[CH:7]=[C:8]([CH:13]=2)[C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1.[OH-].[K+]>CO.C1COCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[CH:7]=[C:8]([CH:13]=2)[C:9]([OH:11])=[O:10])[CH2:2][CH2:3]1.[CH:1]1([C:4]2[CH:5]=[C:6]([CH:7]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:13]=2)[C:14]([OH:16])=[O:15])[CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 57496008HCID 57496008, compound

Product 2

HCID 58531690HCID 58531690, compoundYield 12%HCID 66616530HCID 66616530, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of dimethyl 5-cyclopropylisophthalate (0.8 g, 3.42 mmol) in MeOH (10 mL) and THF (10 mL) was added potassium hydroxide (0.23 g, 4.1 mmol) with stirring. The reaction mixture was heated at 78° C. for 7 h. It was cooled to rt and concentrated in vacuo. To the residue was added a small amount of acetic acid. The mixture was purified by preparative HPLC. The fractions containing the desired product were combined, concentrated and lyophilized to afford 5-cyclopropylisophthalic acid as a white solid (89 mg, 12%) and 3-cyclopropyl-5-(methoxycarbonyl)benzoic acid as a white solid (0.43 g, 56%). 1H NMR (DMSO-d6): δ 13.21 (s, 2H), 8.25 (t, J=1.2 Hz, 1H), 7.85 (d, J=1.2 Hz, 2H), 2.13 (m, 1H), 1.03 (m, 2H), 0.76 (m, 2H).

Workup

  1. temperatureIt was cooled to rt
  2. concentrationconcentrated in vacuo
  3. additionTo the residue was added a small amount of acetic acid
  4. customThe mixture was purified by preparative HPLC
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-973edbec19304f469501925f49c4b47c
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

Loading…