Benzene → Methyl 1,4-dioxaspiro[4.5]decane-8-carboxylate

HRID 1606420Notes

Reaction equation

HRID 1606420 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)([O:3][CH3:4])=[O:2].[CH:12]1[CH:17]=CC=CC=1.C1(C)C=CC(S(O)(=O)=[O:25])=CC=1>C(O)CO>[CH2:17]1[O:25][C:8]2([CH2:9][CH2:10][CH:5]([C:1]([O:3][CH3:4])=[O:2])[CH2:6][CH2:7]2)[O:11][CH2:12]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 226643Methyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10845708Methyl 1,4-dioxaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 189.7 g. of 4-carbomethoxy-1-cyclohexanone [3] (obtained as in Example 2B) in 2000 ml. of benzene, 67.5 ml. of ethylene glycol and 2.7 g. of p-toluenesulfonic acid is heated at reflux under a Dean-Stark trap for about 5 hours. After cooling, the solution is washed with saturated aqueous sodium bicarbonate and brine. The oily residue remaining when the organic solvent is evaporated to dryness and is distilled under vacuum to give 231.8 g. of 4-carbomethoxy-1-cyclohexanone ethylene ketal[4] having a boiling point of 95° to 100° C. at 0.30 mm. of Hg.

Workup

  1. additionA mixture of 189.7 g
  2. temperatureat reflux under a Dean-Stark trap for about 5 hours
  3. temperatureAfter cooling
  4. washthe solution is washed with saturated aqueous sodium bicarbonate and brine
  5. customis evaporated to dryness
  6. distillationis distilled under vacuum
  7. customto give 231.8 g

Sources & evidence

ORD record
ord-bc727e796e42464d8a74f9326d6e4c73
Source dataset
uspto-grants-1976_04
Patent number
US03953425

Reaction notes

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