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

HRID 2250633Notes

Reaction equation

HRID 2250633 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[OH:7][CH2:8][CH2:9][O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

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-4fec2b252ee640fda3b6451af871cc82
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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