Sodium Hydroxide → 4-Benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoic acid

HRID 892190Notes

Reaction equation

HRID 892190 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH:23]=2)[C:12]([C:13]([O:15]CC)=[O:14])=[C:11]([CH3:40])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH:23]=2)[C:12]([C:13]([OH:15])=[O:14])=[C:11]([CH3:40])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22241539Ethyl 4-benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

Product 1

HCID 222414744-Benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate (2.4 g, 4.5 mmole, example 64) is added to ethanol (50 ml) and 11N sodium hydroxide (4.4 ml, 44 mmole) and refluxed for 8 hours. The solvent is removed in vacuo and the residue is dissolved in dichloromethane with a small amount of water and is acidified to pH6 with 1N HCl. The organic layer is dried over MgSO4 and the solvent removed in vacuo. The crude product is purified by column chromatography (silica, 1% methanol in dichloromethane) to provide the title compound. m.p. 146–149° C.; 1H NMR (300 MHz, CD3OD) d 8.34 (d, 1H), 8.04 (d, 1H), 7.91 (d, 1H), 7.78–7.70 (m, 2H), 7.61 (t, H), 7.37–7.20 (m, 7H), 7.05–6.91 (m, 2H), 6.51 (d, 1H), 6.47 (d, 1H), 5.35 (s, 2H), 5.09 (s, 2H), 5.03 (s, 2H), 2.29 (s, 3H); MS (ESI) 506 (M+H)+.

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in dichloromethane with a small amount of water
  4. dry with materialThe organic layer is dried over MgSO4
  5. customthe solvent removed in vacuo
  6. customThe crude product is purified by column chromatography (silica, 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1f8e1727dd384a27a364f2713ba2f2d8
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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