Potassium Hydroxide → 9-(1,3-Benzodioxol-5-yl)-8-methoxycarbonyl-benzo[g][1,3]benzodioxole-7-carboxylic acid

HRID 2354602Notes

Reaction equation

HRID 2354602 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:15](=[C:16]([C:22]3[CH:30]=[CH:29][C:25]4[O:26][CH2:27][O:28][C:24]=4[CH:23]=3)[C:17]=1[C:18]([O:20][CH3:21])=[O:19])[C:11]1[O:12][CH2:13][O:14][C:10]=1[CH:9]=[CH:8]2)=[O:4].[OH-].[K+]>CO>[CH3:21][O:20][C:18]([C:17]1[C:16]([C:22]2[CH:30]=[CH:29][C:25]3[O:26][CH2:27][O:28][C:24]=3[CH:23]=2)=[C:15]2[C:7]([CH:8]=[CH:9][C:10]3[O:14][CH2:13][O:12][C:11]=32)=[CH:6][C:5]=1[C:3]([OH:4])=[O:2])=[O:19]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 5273803Dimethyl 9-(1,3-benzodioxol-5-yl)benzo[g][1,3]benzodioxole-7,8-dicarboxylate

Product 1

HCID 52738049-(1,3-Benzodioxol-5-yl)-8-methoxycarbonyl-benzo[g][1,3]benzodioxole-7-carboxylic acidYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 30 (20 mg, 0.05 mmol) was refluxed with 1 M solution of KOH in MeOH (10 mL) for 2 h. The solution was cooled, and the solvent was removed under reduced pressure. The remaining solid was dissolved in water (10 mL) and then acidified to pH 1-2 with 10% aqueous HCl solution. The precipitate was collected by filtration, washed with water, and dried. The product was purified by column chromatography on silica gel using CH2Cl2/MeOH (20:1 to 10:1, v/v) to give 31 (11 mg, 56%) as a pale yellow powder. mp 273-275° C.; 1H NMR (CDCl3) δ 8.54 (s, 1H, H4), 7.49 (d, 1H, H5, J=8.1 Hz), 7.20 (d, 1H, H6, J=8.1 Hz), 6.76-6.82 (m, 3H, H2′+H5′+H6′), 6.03 (AB, 2H, 3′,4′-OCH2O—, Δδ=11.1 Hz), 5.88 (AB, 2H, 7,8-OCH2O—, Δδ=7.2 Hz), 3.62 (s, 3H, OCH3); MS (FAB, positive) m/z 395 [M+H]+.

Workup

  1. temperatureThe solution was cooled
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe remaining solid was dissolved in water (10 mL)
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5620a471be894c5c91c88f2e13c94fe8
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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