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Carbon Dioxide → 3-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid

HRID 1634
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인쇄 미리보기

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HRID 1634 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]([CH3:19])([CH3:18])[CH2:7][CH2:6][C:5]2([CH3:21])[CH3:20].C([Li])(C)(C)C.[C:27](=[O:29])=[O:28].Cl>O1CCCC1.CCCCC>[CH2:12]([C:11]1[C:2]([C:27]([OH:29])=[O:28])=[CH:3][C:4]2[C:5]([CH3:20])([CH3:21])[CH2:6][CH2:7][C:8]([CH3:19])([CH3:18])[C:9]=2[CH:10]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]
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참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 110786473-Bromo-2-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthaleneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 110125513-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid

시약·촉매·용매 2

HCID 8003
Pentane
용매
HCID 8028Tetrahydrofuran용매

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온도
-78 °C

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.

후처리

  1. extractionextracted several times with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. filtrationThe oily crude product was filtered over silica gel (eluent hexane
  6. customhexane/ethyl acetate=4:1) and recrystallized from hexane

출처 및 근거

ORD 기록
ord-4d21f97b1712426ea5d91e06fbf86981
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05726191

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