Sodium Hydroxide → 5-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylic acid

HRID 606358

Reaction equation

HRID 606358 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]1[CH:13]([C:14]([O:16]CC)=[O:15])[CH:8]1[CH2:7][CH2:6]2.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]1[CH:13]([C:14]([OH:16])=[O:15])[CH:8]1[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23001093ethyl 5-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylate

Product 1

HCID 230011155-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylic acidYield 85.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 5-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylate (0.2 g, 0.8 mmol) was dissolved in 2 ml of methanol and the solution of sodium hydroxide (0.2 g, 50 mmol) in 2 ml of water was added to the reaction mixture and stirred at ambient temperature overnight. The extraction of basic reaction mixture into hexane showed that no starting material present. The reaction mixture was acidified with excess of 3M HCl solution (pH=1), and extracted into ethylacetate (3×15 ml). The combined extracts were washed with water and brine, dried over Na2SO4 and concentrated by rotary evaporation to give 0.15 g of mixture of cis/trans acids as white solid.

Workup

  1. extractionThe extraction of basic reaction mixture into hexane
  2. extractionextracted into ethylacetate (3×15 ml)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-d5c321bffcaa46c6a0a68eb0f3509e92
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Linked notes

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