Reaktion #74886

Reaktionsgleichung

H2SO4

acetyl chloride

2,6,10,10-tetramethyl-1-oxa-spiro[4.5]decan-6-ol

N,N-dimethylaniline

→

product

2,6,10,10-Tetramethyl-1-oxa-spiro[4.5]dec-6-yl acetate

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturto reflux during 3 hours
3. 3
   Temperaturcooled
4. 4
   FiltrationThe reaction mixture was then filtered
5. 5
   Sonstigethe clear filtrate thus obtained
6. 6
   workup.ADDITIONpoured
7. 7
   Sonstigeonto crushed ice
8. 8
   WaschenThe organic layer was then washed with NaHCO3 in water
9. 9
   Sonstigedried
10. 10
    Sonstigeevaporated
11. 11
    workup.DISTILLATIONsubjected to a fractional distillation

Vorschrift

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.

Quelle