Lithium Hydroxide → HCID 67324495, compound

HRID 1397264Notes

Reaction equation

HRID 1397264 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH2:13][CH3:14])[CH:12]=1)[C:6]([O:8]C)=[O:7])#[N:2].[Li+].[OH-]>C1COCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH2:13][CH3:14])[CH:12]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67324020HCID 67324020, compound

Product 1

HCID 67324495HCID 67324495, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

The compound methyl 3-cyano-5-ethylbenzoate (270 mg, 1.42 mmol) was dissolved in THF—H2O (7:3 v/v, 10 mL), solution was cooled to 0° C. and LiOH (59 mg, 1.42 mmol) was added. The reaction mixture was allowed to come to room temperature and stirred for 3 h (monitored by TLC; petroleum ether/EtOAc 1:1). Solvent THF was removed under reduced pressure and the aqueous layer was washed with EtOAc to remove the non-polar impurities. The pH of the aqueous layer was adjusted to 2-3 using 1.5N HCl. The product was extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 3-cyano-5-ethylbenzoic acid (200 mg, yield 80%), which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 8.23 (m, 1H), 8.17 (m, 1H), 7.74 (m, 1H), 2.81 (q, J=7.6 Hz, 2H), 1.32 (t, J=7.6 Hz, 3H).

Workup

  1. customto come to room temperature
  2. customSolvent THF was removed under reduced pressure
  3. washthe aqueous layer was washed with EtOAc
  4. customto remove the non-polar impurities
  5. extractionThe product was extracted with EtOAc
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ee4919d859904ad389765ae912259231
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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