Ethylene Glycol → HCID 15012344, compound

HRID 903198Notes

Reaction equation

HRID 903198 reaction equation
[C:1]([O:4][CH2:5][C:6](=[O:11])[CH2:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2].[CH2:12](O)[CH2:13][OH:14].C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:1]([O:4][CH2:5][C:6]1([CH2:7][CH2:8][CH:9]=[CH2:10])[O:14][CH2:13][CH2:12][O:11]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 22165514HCID 22165514, compound

Product 1

HCID 15012344HCID 15012344, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 15.6 g. (0.1 mole) of 1-acetoxy-5-hexen-2-one, 18.6 g. (0.3 mole) of ethylene glycol in 250 ml. of benzene containing 1.56 g. of p-toluene sulfonic acid monohydrate is heated to reflux using a Dean-Stark water separator. After 2 hours, the reaction mixture is shaken well with 250 ml. of cold water. The aqueous layer is washed with 3×25 ml. of ether. The combined organic layers are dried over anhydrous magnesium sulfate. Evaporation of the solvent gives 2-acetoxymethyl-2-(3-buten-1-yl)-1,3-dioxolane in 90% yield as a light brown oil. ##STR41##

Workup

  1. additionA mixture of 15.6 g
  2. temperatureto reflux
  3. washThe aqueous layer is washed with 3×25 ml
  4. dry with materialThe combined organic layers are dried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cbb50e9ebab1429a9880f09475662ab1
Source dataset
uspto-grants-1980_10
Patent number
US04226866

Reaction notes

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