Toluene → HCID 23050500, compound

HRID 1651370Notes

Reaction equation

HRID 1651370 reaction equation
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].[CH3:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[C:1]([O:5][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH3:6])(=[O:4])[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8134Diethylene Glycol Monomethyl EtherHCID 10110Propiolic AcidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 23050500HCID 23050500, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.3 ml (0.2 mol) of propiolic acid are heated at reflux for 20 hours together with 23.6 ml (0.2 mol) of diethylene glycol monomethyl ether, 1.5 g (8 mmol) of p-toluenesulphonic acid monohydrate and 80 ml of toluene, and the resulting reaction water was distilled off azeotropically and collected in a water separator. After completion of the water separation the reaction mixture was washed in succession with saturated sodium bicarbonate solution and with water. The toluene phase was dried over sodium sulphate and concentrated. The crude product was purified by flash chromatography on 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1). There was obtained 2-(2-methoxyethoxy)ethyl propiolate as a colorless oil.

Workup

  1. distillationwas distilled off azeotropically
  2. customcollected in a water separator
  3. customAfter completion of the water separation the reaction mixture
  4. washwas washed in succession with saturated sodium bicarbonate solution and with water
  5. dry with materialThe toluene phase was dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-a6c1bd05de7c403392766466253858a6
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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