Lithium Hydroxide → 6-Cyanonaphthalene-2-carboxylic acid

HRID 325063Notes

Reaction equation

HRID 325063 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]#[N:16])[CH:11]=2)[CH:6]=1)=[O:4].[Li+].[OH-]>C1COCC1.ClCCl.O>[C:15]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[CH:13]2)#[N:16]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 12433083Methyl 6-cyanonaphthalene-2-carboxylate

Product 1

HCID 124330906-Cyanonaphthalene-2-carboxylic acidYield 86.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21908982Water methylene chlorideSolvent

Procedure

A solution of 6-cyano-naphthalene-2-carboxylic acid methyl ester from Example 96 (2.00 g, 9.47 mmol) in THF (19 mL) and 1M aqueous LiOH (18.94 mL, 18,94 mmol) was vigorously stirred at room temperature for 3 hours. The reaction mixture was then diluted with 150 mL of 1:1 dichloromethane/water, and the organics were discarded. The aqueous material was acidified to pH 2 with 1N HC1, extracted with EtOAc (2×150 mL), extracts dried over MgSO4, and concentrated to provide the desired compound as a white solid (1.61 g, 86%).

Workup

  1. extractionextracted with EtOAc (2×150 mL)
  2. dry with materialextracts dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-614a87542aed44478558343a40daeec6
Source dataset
uspto-grants-2001_04
Patent number
US06221914B1

Reaction notes

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