p-Toluenesulfonic acid → HCID 53660555, compound

HRID 964328Notes

Reaction equation

HRID 964328 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].[CH2:7]([O:9][CH:10]=[CH2:11])[CH3:8].CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1.C(OCC)C>[CH2:7]([O:9][CH:10]([O:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[CH3:11])[CH3:8]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8023Ethyl vinyl etherHCID 66774Methyl Glycolate

Product 1

HCID 53660555HCID 53660555, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl glycolate (0.193 g, 2.15 mmol) in THF (21 ml) was treated with ethylvinyl ether (EVE) (1.03 ml, 10.7 mmol) and a catalytic amount of p-TsOH (41 mg). After stirring for 15 min at 0° C., the mixture was diluted with ethyl ether, washed with saturated NaHCO3 aqueous solution, brine, dried (Na2SO4) and evaporated to give methyl (1-ethoxyethoxy)acetate (0.306 g, 87%).

Workup

  1. washwashed with saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-d33a01bc734c4a69b97fbba329d595ba
Source dataset
uspto-grants-1998_06
Patent number
US05767282

Reaction notes

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