반응 #1730

반응 방정식

carbon dioxide

tert.butyl-lithium

6-bromo-7-hexyl-1,1,4,4-tetramethyl-1, 2,3,4-tetrahydro-naphthalene

hydrochloric acid

→

3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid

용매

pentane

tetrahydrofuran

반응 조건

후처리

1. 1
   추출extracted several times with ethyl acetate
2. 2
   세척washed with water
3. 3
   건조dried over sodium sulfate
4. 4
   기타evaporated
5. 5
   여과The oily crude product was filtered over silica gel (eluent hexane
6. 6
   기타hexane/ethyl acetate=4:1) and recrystallized from hexane

실험 절차

15 g of 6-bromo-7-hexyl-1,1,4,4-tetramethyl-1, 2,3,4-tetrahydro-naphthalene were dissolved in 180 ml of tetrahydrofuran and treated dropwise at -78° C. with 64.5 ml of a 1.5 molar solution of tert.butyl-lithium in pentane. After stirring at -78° C. for 1 hour, a carbon dioxide stream was conducted vigorously into the reaction vessel for 2 hours. Subsequently, the reaction mixture was acidified by the addition of 190 ml of 2N hydrochloric acid, extracted several times with ethyl acetate, washed with water, dried over sodium sulfate and evaporated. The oily crude product was filtered over silica gel (eluent hexane, then hexane/ethyl acetate=4:1) and recrystallized from hexane. There were obtained 7.6 g of 3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid in colorless crystals, m.p. 98°-99° C.

출처