Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 20762880, compound

HRID 860489Notes

Reaction equation

HRID 860489 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][O:5][CH2:6][CH2:7][O:8]C1CCCCO1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][O:5][CH2:6][CH2:7][OH:8]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 85982055HCID 85982055, compound

Product 1

HCID 20762880HCID 20762880, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]acetate (1.07 g) and pyridinium p-toluenesulfonate (24.6 mg) in MeOH (10 mL) was heated under reflux for 2 hours. After evaporation of solvent, the residue was purified by silica gel column chromatography eluting with a mixture of hexane and AcOEt (10:1-1:3) to give methyl(2-hydroxyethoxy)acetate as colorless oil (555 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of solvent
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with a mixture of hexane and AcOEt (10:1-1:3)

Sources & evidence

ORD record
ord-a69473a852bd443ab23567d37d2c711d
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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