Reaktion #2688

Reaktionsgleichung

NaOH

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole

n-butyllithium

carbon dioxide

→

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-carboxylic acid

Lösungsmittel

Water

THF

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   SonstigeAfter attaining ambient temperature
3. 3
   WaschenAfter washing with ether
4. 4
   Extraktionextracted with ether (2*300 mL)
5. 5
   TrocknenThe organic phases were dried (Na2SO4)
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give the pure product

Vorschrift

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole (10.0 g, 45.0 mmol; prepared according to WO-91/12024) was dissolved in dry THF (200 mL) under an argon atmosphere. The solution was cooled to -20° C. and n-butyllithium (20.0 mL, 50.0 mmol) in hexane was added. After attaining ambient temperature, the reaction mixture was transferred onto solid carbon dioxide (150 g) and allowed to stand overnight. Water (200 mL) was added and pH was adjusted to 10 using 2M aqueous NaOH. After washing with ether, the aqueous phase was acidified with 2M hydrochloric acid to pH 2 and extracted with ether (2*300 mL). The organic phases were dried (Na2SO4) and evaporated to give the pure product.

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