Methanol → HCID 59710724, compound
Reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:18])[C:6]1[CH:15]=[CH:14][CH:13]=[C:8]([C:9]([O:11]C)=[O:10])[C:7]=1[O:16][CH3:17].[CH3:19]O>>[CH3:19][C:14]1[CH:13]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([O:16][CH3:17])=[C:6]([CH:15]=1)[C:5]([OH:4])=[O:18]Participants
Procedure
An aqueous solution of sodium hydroxide (5M, 100 mL) was added under cooling to a solution of 5 (0.5 mol) in methanol (1.5 L). The mixture was stirred for 3 days at room temperature. The solvents were removed under reduced pressure and the residue dissolved in hot acetone (2 L). A thick paste precipitated from the acetone solution overnight (room temperature). TLC reveals that the upper acetone solution mainly contained the starting diester and the mono-sodium salt of the acid and that the lower paste was a mixture of the mono- and disodium salt of the acid. Acetone was removed from both fractions and the chromatographic separation on a gradient flash silica gel column (0-3% methanol in CH2Cl2) of both fractions gave 40 g the desired product. Yield 63%. 1H NMR (500 MHz, CDCl3, 25° C.), δ: 3.913 (s, 3H, OCH3), 3.982 (s, 3H OCH3), 7.252 (t, J=7.75, 1H, ArH), 7.991 (d, J=7.5, 1H, ArH), 8.166 (d, J=7.5, 1H, ArH). 13C NMR (500 MHz, CDCl3, 25° C.), δ: 52.48, 64.09, 124.10, 125.67, 136.38, 136.49, 159.76, 165.46, 167.69.
Workup
- customThe solvents were removed under reduced pressure
- dissolutionthe residue dissolved in hot acetone (2 L)
- customA thick paste precipitated from the acetone solution overnight (room temperature)
- additiona mixture of the mono- and disodium salt of the acid
- customAcetone was removed from both fractions
- customthe chromatographic separation on a gradient flash silica gel column (0-3% methanol in CH2Cl2) of both fractions
Sources & evidence
- ORD record
- ord-239de3895cc3468db2fded26ce7864d6
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06406297B1
Reaction notes
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