Methanol → HCID 11117771, compound

HRID 2301279Notes

Reaction equation

HRID 2301279 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13]#[N:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:15]([O:17]C)=[O:16].O[Li].O.O.CO>C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3]1[C:12]([C:13]#[N:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 11746770methyl 2-methoxy-3-cyano-1-naphthoate

Product 1

HCID 11117771HCID 11117771, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of methyl 2-methoxy-3-cyano-1-naphthoate (0.113 g) and LiOH.H2O (0.0196 g) THF (3 mL), water (1 mL) and methanol (1 mL) was stirred overnight at room temperature. The solution was diluted with saturated sodium bicarbonate and extracted with Et2O. The aqueous layer was acidified to pH 2 by addition of 1N HCl and extracted with Et2O. The organic layer was washed with water (30 mL) and brine (40 mL), dried (sodium sulfate), filtered, and concentrated to a white solid. 1H NMR (DMSO-d6): δ14.06 (broad, 1 H), 8.08-8.02 (m, 1 H), 7.83-7.76 (m, 2 H), 7.69-7.63 (m, 1 H), 4.02 (s, 3 H); MS m/z: 226 (M−1).

Workup

  1. extractionextracted with Et2O
  2. additionThe aqueous layer was acidified to pH 2 by addition of 1N HCl
  3. extractionextracted with Et2O
  4. washThe organic layer was washed with water (30 mL) and brine (40 mL)
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-ee3f6a43260940f09d7b483ce553a142
Source dataset
uspto-grants-2002_12
Patent number
US06500818B1

Reaction notes

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