Allyl bromide → 2,6,6-Trimethyl-1-(1-hydroxy-3-butenyl)-1-cyclohexene

HRID 903286

反応式

HRID 903286 の反応式
[CH2:1](Br)[CH:2]=[CH2:3].[CH3:5][C:6]1[CH2:11][CH2:10][CH2:9][C:8]([CH3:13])([CH3:12])[C:7]=1[CH:14]=[O:15].[NH4+].[Cl-]>CCOCC>[CH3:5][C:6]1[CH2:11][CH2:10][CH2:9][C:8]([CH3:12])([CH3:13])[C:7]=1[CH:14]([OH:15])[CH2:3][CH:2]=[CH2:1]

参加物

5

反応物 3

HCID 7841Allyl bromide2 回HCID 9895beta-CyclocitralHCID 25517Ammonium Chloride

生成物 1

HCID 124203212,6,6-Trimethyl-1-(1-hydroxy-3-butenyl)-1-cyclohexene収率 57%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

実験手順

In a typical experiment 10.7 g. of Mg turnings and 5 g. of allyl bromide were allowed to react in 7: ml. of dry ether. The reaction was exothermic and the temperature of the reaction mixture increased up to the boiling point of the solvent. To this solution allyl bromide (46 g.) and β-cyclocitral (61 g.) in 160 ml. of ether were added with vigorous stirring at such a rate as to maintain the ether at the boiling temperature. The reaction mixture was then kept at reflux during 6 hours and after cooling it was poured into a ice-cold concentrated aqueous solution of NH4Cl. The ethereal layer after the usual treatment gave 2,6,6-trimethyl-1-[1-hydroxy-3-butenyl]-1-cyclohexene (44.5 g.; 57% yield): B.p. 60°-2°/0.001 Torr; nD20 =1.4964; d420 =0.9.

後処理

  1. customto react in 7
  2. temperaturethe temperature of the reaction mixture increased up to the boiling point of the solvent
  3. temperatureat reflux during 6 hours
  4. temperatureafter cooling it

出典と根拠

ORDレコード
ord-3d4998c29d784fe4b111ac6f55acef77
出典データセット
uspto-grants-1980_10
特許番号
US04226892

関連ノート

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