Propargyl alcohol → HCID 19736363、化合物

HRID 326217ノート

反応式

HRID 326217 の反応式
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[CH2:10][CH2:11][C:12](=[O:14])[CH3:13].[CH2:15]([OH:18])[C:16]#[CH:17].[OH-].[K+].[NH4+].[Cl-]>C1COCC1.O>[CH3:13][C:12]([OH:14])([CH2:11][CH2:10][C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])[C:17]#[C:16][CH2:15][OH:18]

参加物

7

反応物 4

HCID 7859Propargyl alcoholHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 519382Dihydro-beta-ionone

生成物 1

HCID 19736363HCID 19736363、化合物収率 80%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

A mixture of 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone (107 g, 0.55 mol) and propargyl alcohol (34 g, 0.61 mol) was added dropwise during 1.5 h to a mechanically stirred slurry of powered KOH (Fluka, 230 g, 4.1 mol) in THF (tetrahydrofuran 800 ml) maintained at 20° C. After a further 3 h, the brown mixture was poured into a cold solution of NH4Cl (250 g, 4.7 mol) in H2O (800 ml) and the phases separated. Extraction of the aqueous phase with ether and concentration of the combined organic phase afforded a reddish brown solid which was recrystallized from petroleum ether (80/100) to furnish 4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-hexyn-1,4-diol as a pale yellow powder (110 g, 80% yield).

後処理

  1. customthe phases separated
  2. extractionExtraction of the aqueous phase with ether and concentration of the combined organic phase
  3. customafforded a reddish brown solid which
  4. customwas recrystallized from petroleum ether (80/100)

出典と根拠

ORDレコード
ord-00d63733f46d46a6b7d1b2e0815978e9
出典データセット
uspto-grants-1993_12
特許番号
US05268355

反応ノート

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