Ethylene Glycol → Methyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate

HRID 1462922Notes

Reaction equation

HRID 1462922 reaction equation
[CH3:1][C:2]1([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH2:13](O)[CH2:14][OH:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:13]1[CH2:14][O:15][C:5]2([CH2:4][CH2:3][C:2]([CH3:1])([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6]2)[O:8]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 12568255Methyl 1-methyl-4-oxocyclohexane-1-carboxylate

Product 1

HCID 22591390Methyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl 1-methyl-4-oxocyclohexanecarboxylate (30 g) was dissolved in benzene (300 ml). Ethylene glycol (30 ml) and p-toluenesulfonic acid monohydrate (1 g) were added, and the mixture was refluxed for 4 hours. The water which formed during the heating was removed by using a water trap. After cooling, the mixture was washed with water and dryed (MgSO4). The solvent was distilled off to give methyl 4,4-ethylenedioxy-1-methylcyclohexanecarboxylate as an oil (37.8 g, 100%).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customwas removed
  3. temperatureAfter cooling
  4. washthe mixture was washed with water
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-2f9cab8403a347f594ea664526428688
Source dataset
uspto-grants-1984_07
Patent number
US04461902

Reaction notes

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