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

HRID 2354592Notes

Reaction equation

HRID 2354592 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:21](=[C:22]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[C:23]=1[CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:17]1[O:18][CH2:19][O:20][C:16]=1[CH:15]=[CH:14]2)=[O:10])C1C=CC=CC=1.[OH-].[Na+]>CO.O>[O:37]1[C:36]2[CH:40]=[CH:41][C:33]([C:22]3[C:23]([CH2:24][O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[C:11]([C:9]([OH:10])=[O:8])[CH:12]=[C:13]4[C:21]=3[C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=[CH:14]4)=[CH:34][C:35]=2[O:39][CH2:38]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5273778Benzyl 9-(1,3-benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylate

Product 1

HCID 52737799-(1,3-Benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 4 (56 mg, 0.11 mmol) and NaOH (16 mg, 0.4 mmol) in MeOH/H2O (4:1, 2 mL) was heated at 70° C. for 12 h. The solvent was evaporated to dryness, and the residue was dissolved in water. The aqueous solution was acidified to pH 1-2 with 10% aqueous HCl solution and then extracted with ether (3×50 mL). The extract was washed with water and brine, and dried over MgSO4. The evaporation of solvent yielded 5 (32 mg, 70%) as a white powder. mp 219-221° C.; 1H NMR (DMSO-d6) δ 8.27 (s, 1H, H4), 7.70 (d, 1H, H5, J=8.7 Hz), 7.38 (d, 1H, H6, J=8.7 Hz), 7.17-7.25 (m, 5H, OCH2Ph), 6.89 (d, 1H, H5′, J=8.1 Hz), 6.79 (d, 1H, H2′, J=1.5 Hz), 6.65 (dd, 1H, H6′, J=1.5, 8.1 Hz), 6.06 (AB, 2H, 3′,4′-OCH2O—, Δδ=18.0 Hz, J=0.6 Hz), 5.85 (AB, 2H, 7,8-OCH2O—, Δδ=9.3 Hz, J=0.9 Hz), 4.53 (s, 2H, 2-CH2OCH2Ph), 4.24 (s, 2H, 2-CH2OBn); MS (FAB, positive) m/z 457 [M+H]+.

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ether (3×50 mL)
  4. washThe extract was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customThe evaporation of solvent

Sources & evidence

ORD record
ord-560dfcdc4b0148b2853e0032ff2eae4c
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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