Propargyl alcohol → HCID 19736363, 화합물

HRID 326217노트

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HRID 326217 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 19736363HCID 19736363, 화합물수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
20 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-00d63733f46d46a6b7d1b2e0815978e9
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05268355

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