Ethylene Glycol → HCID 53973528, compound

HRID 893362Notes

Reaction equation

HRID 893362 reaction equation
[CH:1]([CH2:3][C:4]([CH3:12])([CH3:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2].[CH2:13](O)[CH2:14][OH:15].O>C1(C)C=CC=CC=1>[O:8]1[CH2:9][CH2:10][O:7][CH:6]1[CH2:5][C:4]([CH3:11])([CH3:12])[CH2:3][C:1]([O:15][CH2:14][CH3:13])=[O:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 13050815Ethyl 4-formyl-3,3-dimethylbutanoate

Product 1

HCID 53973528HCID 53973528, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

74 g of ethyl 4-formyl-3,3-dimethylbutanoate, prepared in Example 91, are dissolved in 450 ml of anhydrous toluene in the presence of 0.5 g of paratoluenesulfonic acid and 26.7 g of ethylene glycol. The mixture is heated to the reflux temperature and the water formed during the reaction is removed by means of a Dean-Stark apparatus. After refluxing for two hours, the solvent is evaporated off under vacuum and the residue is distilled to give 86.7 g of ethyl 4-(dioxolan-2-yl)-3,3-dimethylbutanoate in the form of a liquid with a boiling point b.p. 10 of 138°-140° C.

Workup

  1. temperatureThe mixture is heated to the reflux temperature
  2. customis removed by means of a Dean-Stark apparatus
  3. temperatureAfter refluxing for two hours
  4. customthe solvent is evaporated off under vacuum
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-139a9648da9a4799ad287c590106c214
Source dataset
uspto-grants-1992_06
Patent number
US05124336

Reaction notes

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