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

HRID 1606420

Reaktionsgleichung

Reaktionsgleichung von HRID 1606420
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bc727e796e42464d8a74f9326d6e4c73
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03953425

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