Lithium hydroxide, monohydrate → (2-Chloro-4-cyano-5-methoxyphenyl)acetic acid

HRID 2173340Notes

Reaction equation

HRID 2173340 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]([O:15]C)=[O:14].O[Li].O>C1COCC1.CO.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 77231255Methyl (2-chloro-4-cyano-5-methoxyphenyl)acetate

Product 1

HCID 67513894(2-Chloro-4-cyano-5-methoxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a mixture of methyl (2-chloro-4-cyano-5-methoxyphenyl)acetate (30 mg, 0.125 mmol) in 15 mL of THF/MeOH/H2O (V/V/V=2:2:1) was added LiOH H2O (11 mg, 0.250 mmol). The mixture was stirred at rt. For 1 hr, and then most of the solvent was concentrated. The residue was diluted with water, adjusted pH=3 with 3 N HCl, and then extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated to give (2-chloro-4-cyano-5-methoxyphenyl)acetic acid. 1H-NMR (400 MHz, CDCl3) δ ppm 7.56 (s, 1H), 6.91 (s, 1H), 3.92 (s, 3H), 3.83 (s, 2H).

Workup

  1. concentrationmost of the solvent was concentrated
  2. additionThe residue was diluted with water, adjusted pH=3 with 3 N HCl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e6bf5de0f81c41ed83c68fdb5ff398d0
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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