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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
ノート
印刷プレビュー

反応式

HRID 1634 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8003
Pentane
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4d21f97b1712426ea5d91e06fbf86981
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05726191

反応ノート

読み込み中…

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