Sodium Hydroxide → 3-Cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

HRID 2185888Notes

Reaction equation

HRID 2185888 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([O:15]C)=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].[OH-].[Na+]>C1COCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([OH:15])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22452655Methyl 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

Product 1

HCID 224526443-Cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acidYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (0.96 g, 4.46 mmol) in THF (54 mL), water (21 mL) and 1N NaOH (9.4 mL, 9.4 mmol) was stirred overnight at room temperature. The THF was removed in vacuo and the mixture acidified to pH 1with 1N HCl. The resulting precipitate was extracted with EtOAc, dried (MgSO4), filtered and concentrated to give the title compound as a white solid (0.88 g, 98%). 1H NMR (DMSO) δ 13.33 (s, 1H), 7.96 (d, 1H), 7.29 (d, 1H), 3.99 (d, 2H), 2.81 (d, 2H), 1.72 (m, 4H); MS m/z 200.1 (M−H).

Workup

  1. customThe THF was removed in vacuo
  2. extractionThe resulting precipitate was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6d21d6da627c43709fb64a9ce32a8289
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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