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

HRID 2354603Notes

Reaction equation

HRID 2354603 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]C)=[O:19])[C:11]1[O:12][CH2:13][O:14][C:10]=1[CH:9]=[CH:8]2)=[O:4].[OH-].[K+].COC(C1C(C2C=CC3OCOC=3C=2)=C2C(C=CC3OCOC=32)=CC=1C(O)=O)=O>CO>[O:26]1[C:25]2[CH:29]=[CH:30][C:22]([C:16]3[C:17]([C:18]([OH:20])=[O:19])=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[C:7]4[C:15]=3[C:11]3[O:12][CH2:13][O:14][C:10]=3[CH:9]=[CH:8]4)=[CH:23][C:24]=2[O:28][CH2:27]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 5273803Dimethyl 9-(1,3-benzodioxol-5-yl)benzo[g][1,3]benzodioxole-7,8-dicarboxylateHCID 52738049-(1,3-Benzodioxol-5-yl)-8-methoxycarbonyl-benzo[g][1,3]benzodioxole-7-carboxylic acid

Product 1

HCID 52738059-(1,3-Benzodioxol-5-yl)benzo[g][1,3]benzodioxole-7,8-dicarboxylic acidYield 63.1%

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 24 h. Completion of the reaction, followed by the workup as described for the isolation of 31, gave a residue, which was purified by silica gel column chromatography. Elution with CH2Cl2/MeOH (2:1, v/v) as eluent yielded 32 (12 mg, 63%) as a yellow powder. mp 253° C. (decomp.); 1H NMR (DMSO-d6) δ 8.25 (s, 1H, H4), 7.53 (d, 1H, H5, J=8.7 Hz), 7.24 (d, 1H, H6, J=8.7 Hz), 6.72-6.82 (m, 3H, H2′+H5′+H6′), 5.99 (AB, 2H, 3′,4′-OCH2O—, Δδ=18.9 Hz), 5.81 (AB, 2H, 7,8-OCH2O—, Δδ=6.0 Hz); MS (FAB, positive) m/z 381 [M+H]+.

Workup

  1. customCompletion of the reaction
  2. customgave a residue, which
  3. customwas purified by silica gel column chromatography
  4. washElution with CH2Cl2/MeOH (2:1

Sources & evidence

ORD record
ord-373d6235d470462b9df8c93176e4c8de
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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