Potassium Iodide → 4-tert-Butoxycarbonylmethoxy-3-methyl-benzoic Acid Methyl Ester

HRID 220846Notes

Reaction equation

HRID 220846 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:9]([O:13][C:14](=[O:17])[CH2:15]Br)([CH3:12])([CH3:11])[CH3:10].[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:28])[CH:22]=1>CC(C)=O>[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:15][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:17])=[C:23]([CH3:28])[CH:22]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 11240684Methyl 4-hydroxy-3-methylbenzoate

Product 1

HCID 575554074-tert-Butoxycarbonylmethoxy-3-methyl-benzoic Acid Methyl EsterYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (4.6 g, 33 mmol), potassium iodide (0.25 g, 1.5 mmol) and tert-butylbromoacetate (2.5 ml, 16.5 mmol) were added to a solution of 4-hydroxy-3-methyl-benzoic acid methyl ester from Example E29 (2.5 g, 15 mmol) in acetone (150 ml) and the mixture was heated at reflux for 20 h. The solid was filtered off and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc, washed with 1N KHSO4, water then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane) to yield the title compound (3.8 g, 90%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 20 h
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with 1N KHSO4, water
  7. dry with materialbrine, dried
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane)

Sources & evidence

ORD record
ord-762dd763ee104b21830661a0cc457235
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

Loading…