Toluene → HCID 23050500, compound

HRID 1651831Notes

Reaction equation

HRID 1651831 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.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

5

Reactant 3

HCID 1140TolueneHCID 8134Diethylene Glycol Monomethyl EtherHCID 10110Propiolic Acid

Product 1

HCID 23050500HCID 23050500, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.3 ml (0.2 mol) of propiolic acid were boiled 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, with the resulting reaction water being distilled off azeotropically and being 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. distillationdistilled off azeotropically
  2. custombeing collected 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-6afcc10252804faeba4711756a41ed96
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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