Water → (+/-)-6-[2-(1,2-Epoxy-2,6,6-trimethylcyclohexanyl)ethynyl]naphthoic acid
Reaction equation
[C:1]([O:12][O-])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([O-])=O.[Mg+2].[OH2:15].[CH3:16][C:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]=1[C:25]#[C:26][C:27]1[CH:28]=C2C(=C[CH:36]=1)C=C(C(O)=O)C=C2>C(O)(C)C.[Cl-].[Na+].O>[O:15]1[C:17]2([CH3:16])[CH2:22][CH2:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]12[C:25]#[C:26][C:27]1[CH:28]=[C:7]2[C:3](=[CH:4][CH:36]=1)[C:2]([C:1]([OH:12])=[O:11])=[CH:10][CH:9]=[CH:8]2Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of 0.135 g (0.218 mmol) of 80% magnesium monoperoxyphthalate acid (MMPP) and 2 ml iso-propyl alcohol was added enough water (0.20 ml) to just dissolve the solid. This solution was added to a solution of 0.058 g (0.182 mmol) of 6-[2-(2,6,6-trimethylcyclohex-1-enyl)ethynyl]-2-naphthoic acid (Compound 4) in 1 ml iso-propyl alcohol and stirred at ambient temperature for 3 days. The solution was treated with 2 ml of brine and extracted with 3×10 ml ethyl acetate. The organic extracts were combined and washed with 5 ml saturated aqueous NaCl and dried (MgSO4). The solvent was removed in-vacuo and the residue purified by flash chromatography (SiO2, 75:25 ethyl acetate in hexanes) to give the title compound as a white solid
Workup
- dissolutionto just dissolve the solid
- extractionextracted with 3×10 ml ethyl acetate
- washwashed with 5 ml saturated aqueous NaCl
- dry with materialdried (MgSO4)
- customThe solvent was removed in-vacuo
- customthe residue purified by flash chromatography (SiO2, 75:25 ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-43dce4bf1b404f90ad3da341b9b07cc5
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05451605
Reaction notes
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