Lithium Hydroxide → (4-Cyanonaphthalen-1-yl)acetic acid

HRID 132690Notes

Reaction equation

HRID 132690 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]#[N:16])=[CH:7][CH:6]=1.[Li+].[OH-]>CO>[C:15]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([CH2:4][C:3]([OH:17])=[O:2])=[CH:6][CH:7]=1)#[N:16]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59734598Methyl 2-(4-cyanonaphthalen-1-yl)acetate

Product 1

HCID 12433025(4-Cyanonaphthalen-1-yl)acetic acidYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 2A (6.20 g, 26.7 mmol) in MeOH (100 mL) was treated with saturated aqueous LiOH (15 mL), and the reaction mixture was stirred at rt overnight (˜16 h). The resulting mixture was concentrated in vacuo to dryness and partitioned between a mixed solvent (50% Et2O:50% EtOAc) and H2O. The H2O layer was acidified to pH 2-3 and extracted with EtOAc (3×20 mL). The EtOAc was dried over Na2SO4 and concentrated in vacuo to give a yellow solid (2.1 g) in 38% yield.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo to dryness
  2. custompartitioned between a mixed solvent (50% Et2O:50% EtOAc) and H2O
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe EtOAc was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-534ee3c0e1fe4206914c3ccaa4723212
Source dataset
uspto-grants-2008_06
Patent number
US07388027B2

Reaction notes

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