HCID 44157527, compound → 2,3-Bis(4-methoxybenzyloxy)benzoic acid

HRID 2273674

Reaction equation

HRID 2273674 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[CH:37][C:6]([CH2:7][O:8][C:9]2[C:26]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH:25][CH:24]=[CH:23][C:10]=2[C:11]([O:13]CC2C=CC(OC)=CC=2)=[O:12])=[CH:5][CH:4]=1>O1CCOCC1.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[C:26]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)=[CH:25][CH:24]=[CH:23][C:10]=2[C:11]([OH:13])=[O:12])=[CH:37][CH:38]=1

Participants

4

Reactant 1

HCID 44157527HCID 44157527, compound

Product 1

HCID 216602332,3-Bis(4-methoxybenzyloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 19 (8.60 g, 16.71 mmol) in dioxane (84 mL) and 2N NaOH (42 mL) was stirred for 24 h at room temperature. The reaction mixture was concentrated in vacuo. The residue was stirred with H2O (100 mL) and then acidified to pH 2 with 1N HCl. The white solid was filtered, washed with hexane, and was recrystallised from EtOAc/hexanes to generate 5.93 g (90%) of 20 as a white crystalline solid, mp 129° C.: 1H NMR δ 3.8 (s, 3H), 3.85 (s, 3H), 5.12 (s, 2H), 5.20 (s, 2H), 6.83 (d, 2H, J=8.8), 6.96 (d, 2H, J=9.2), 7.18 (t, 2H, J=8.0), 7.22-7.27 (m, 2H), 7.41 (d, 2H, J=8.4), 7.73 (dd, 1H, J=1.2, 8.0); 13C NMR δ 55.36, 55.37, 55.44, 55.46, 71.42, 114.26, 119.12, 123.04, 124.37, 125.00, 126.87, 128.02, 129.73, 131.21, 147.17, 151.45, 159.94, 160.44, 165.45; HRMS m/z calcd for C23H22NaO6, 417.1332 (M+Na). found, 417.1332.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe white solid was filtered
  3. washwashed with hexane
  4. customwas recrystallised from EtOAc/hexanes

Sources & evidence

ORD record
ord-99d6e2f20e9d4a75ad053d1b129c6fd4
Source dataset
uspto-grants-2015_09
Patent number
US09125950B2

Linked notes

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