Sodium Hydroxide → HCID 22452645, compound

HRID 2185891Notes

Reaction equation

HRID 2185891 reaction equation
[CH3:1][O:2][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.[OH-].[Na+]>C1COCC1.O>[CH3:1][O:2][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

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22452670HCID 22452670, compound

Product 1

HCID 22452645HCID 22452645, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-methoxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (0.90 g, 4.09 mmol) in THF (50 mL), water (20 mL) and 1N NaOH (8.6 mL, 8.6 mmol) was stirred for 3 days at room temperature. The THF was evaporated and the mixture acidified to pH 1 with 1N HCl. The resulting precipitate was extracted with EtOAc, dried (MgSO4), filtered and concentrated to give the acid as a white solid (0.80 g, 95%). 1H NMR (DMSO) δ 12.79 (s, 1H), 7.09 (d, 1H), 6.82 (d, 1H), 3.73 (s, 3H), 2.86 (s, 2H), 2.74 (s, 2H), 1.68 (m, 4H); MS m/z 205 (M−H).

Workup

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

Sources & evidence

ORD record
ord-5a656a71bc7a431cb293f435048fffa1
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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