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Ammonium Chloride → 1-[4-(Hydroxy-3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

HRID 1071916
ノート
印刷プレビュー

反応式

HRID 1071916 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:17]C)(OC)[CH3:14])=[CH:9][CH:8]=1.[CH3:19][C:20]1([CH3:29])[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22](=[O:28])[CH2:21]1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[OH:28][C:22]1([C:7]2[CH:8]=[CH:9][C:10]([C:13](=[O:17])[CH3:14])=[CH:11][CH:12]=2)[CH2:23][C:24]([CH3:27])([CH3:26])[CH2:25][C:20]([CH3:29])([CH3:19])[CH2:21]1
参加物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 25517Ammonium ChlorideHCID 843993,3,5,5-TetramethylcyclohexanoneHCID 109117821-Bromo-4-(1,1-dimethoxyethyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 223904201-[4-(Hydroxy-3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone収率 88%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8058Hexane溶媒

実験手順

27.5 ml of a 1.6 M solution of n-butyllithium in hexane are added dropwise at −78° C. to a solution of 10 g of 1-bromo-4-(1,1-dimethoxyethyl)benzene (compound Vp) in 100 ml of tetrahydrofuran. The reaction mixture is stirred for 2 hours at this temperature. A solution of 6.92 ml of 3,3,5,5-tetramethylcyclohexanone in 20 ml of tetrahydrofuran is added over 20 minutes and the reaction mixture is stirred at −78° C. for 1 hour. After warming to room temperature, 140 ml of saturated aqueous ammonium chloride solution are added. The phases are separated after settling has taken place, the aqueous phase is extracted with diethyl ether, the organic phases are combined and dried over magnesium sulphate, and the solvents are evaporated off under reduced pressure. The oil obtained is purified by chromatography on a column of silica gel, eluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture; yield=88%; m.p.=135° C. The following compounds are prepared in the same way:

後処理

  1. stirringthe reaction mixture is stirred at −78° C. for 1 hour
  2. customThe phases are separated after settling
  3. extractionthe aqueous phase is extracted with diethyl ether
  4. dry with materialdried over magnesium sulphate
  5. customthe solvents are evaporated off under reduced pressure
  6. customThe oil obtained
  7. customis purified by chromatography on a column of silica gel
  8. washeluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture
  9. customThe following compounds are prepared in the same way

出典と根拠

ORDレコード
ord-5460a4871551449fa5fe5f6c1f2cdb05
出典データセット
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06908914B1

反応ノート

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