N,N-Dimethylaniline → 1-Oxaspiro[4.5]decan-6-ol, 2,6,10,10-tetramethyl-, 6-acetate

HRID 597613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597613
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][CH:6]1[CH2:10][CH2:9][C:8]2([C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]2([CH3:19])[OH:18])[O:7]1.CN(C)C1C=CC=CC=1.OS(O)(=O)=O>CCOCC>[C:1]([O:18][C:11]1([CH3:19])[CH2:12][CH2:13][CH2:14][C:15]([CH3:17])([CH3:16])[C:8]21[O:7][CH:6]([CH3:5])[CH2:10][CH2:9]2)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 949N,N-DimethylanilineHCID 1118Sulfuric AcidHCID 6367Acetyl chlorideHCID 654286-Hydroxydihydrotheaspirane

Produkt 1

HCID 938381-Oxaspiro[4.5]decan-6-ol, 2,6,10,10-tetramethyl-, 6-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

5.9 g (0.079 M) of acetyl chloride were added over 30 minutes at 20° to a mixture of 2,6,10,10-tetramethyl-1-oxa-spiro[4.5]decan-6-ol -- isomer A; see Example 1 -- and 10.9 g of N,N-dimethylaniline. After having been kept for 2 days at room temperature the reaction mixture was heated to reflux during 3 hours, then cooled and treated with 50 ml of ether. The reaction mixture was then filtered and the clear filtrate thus obtained poured onto crushed ice and finally acidified with a 10 % aqueous solution of H2SO4. The organic layer was then washed with NaHCO3 in water, dried, evaporated and subjected to a fractional distillation to give 2.5 g of a product having b.p. 90° - 100°/0.1 Torr. After crystallisation in aqueous ethanol 1.9 g (75%) of the desired ester were isolated -- isomer A.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux during 3 hours
  3. temperaturecooled
  4. filtrationThe reaction mixture was then filtered
  5. customthe clear filtrate thus obtained
  6. additionpoured
  7. customonto crushed ice
  8. washThe organic layer was then washed with NaHCO3 in water
  9. customdried
  10. customevaporated
  11. distillationsubjected to a fractional distillation

Quellen und Nachweise

ORD-Eintrag
ord-faeb7ce7dbb7442484f5adf7898eb507
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04014905

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