Sodium Hydroxide → 1-Methyl 5-(phenylmethoxy)-1,3-benzenedicarboxylate

HRID 852545Notes

Reaction equation

HRID 852545 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 7643390Dimethyl 5-bentyloxy-isophthalate

Product 1

HCID 214406211-Methyl 5-(phenylmethoxy)-1,3-benzenedicarboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-benzyloxy-isophthalic acid dimethyl ester (D44) (24 g, 80 mmol, 1 equiv) in MeOH (300 ml) was added 1N aqueous NaOH solution (76 ml, 76 mmol, 0.95 equiv) and the resulting solution was stirred at room temperature for 17 h. A second portion of 1N aqueous NaOH solution (15 ml, 15 mmol, 0.2 equiv) was added and the solution stirred for another 6 h. Most of the MeOH was removed in vacuo and the residue was partitioned between AcOEt and 1N aqueous NaOH solution. The aqueous layer was extracted with AcOEt, acidified to pH 1 and re-extracted with AcOEt. The second organic extract was dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O to give 5-benzyloxy-isophthalic acid monomethyl ester (D46) (15.5 g, 68%) as a white solid. [M+H]+=2.86.0, RT=3.32 min

Workup

  1. stirringthe solution stirred for another 6 h
  2. customMost of the MeOH was removed in vacuo
  3. customthe residue was partitioned between AcOEt and 1N aqueous NaOH solution
  4. extractionThe aqueous layer was extracted with AcOEt
  5. extractionre-extracted with AcOEt
  6. extractionThe second organic extract
  7. dry with materialwas dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-8f9185061e254d3a8cc15bf03b7dd640
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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