Diethyl Sulfate → Cyclohexene, 2-(3-ethoxy-1-buten-1-yl)-1,3,3-trimethyl-

HRID 1462835ノート

反応式

HRID 1462835 の反応式
S(OCC)(O[CH2:5][CH3:6])(=O)=O.[CH3:10][C:11]1[CH2:16][CH2:15][CH2:14][C:13]([CH3:18])([CH3:17])[C:12]=1/[CH:19]=[CH:20]/[CH:21]([OH:23])[CH3:22].[H-].[Na+]>>[CH3:5][CH2:6][O:23][CH:21](/[CH:20]=[CH:19]/[C:12]1[C:13]([CH3:17])([CH3:18])[CH2:14][CH2:15][CH2:16][C:11]=1[CH3:10])[CH3:22]

参加物

4

反応物 3

HCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 5373729(3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-ol

生成物 1

HCID 6436993Cyclohexene, 2-(3-ethoxy-1-buten-1-yl)-1,3,3-trimethyl-

実験手順

74.0 g (0.48 mol) of diethyl sulphate were added dropwise to a suspension of β-ionol alcoholate [obtained from 65.8 g (0.34 mol) of β-ionol and 18.4 g (ca 0.44 mol) of 55%-60% sodium hydride in 600 ml of benzene] in such a manner that the temperature did not exceed 50° C. Subsequently, the mixture was stirred at reflux for 3 hours, cooled and worked-up as described in Example 1. Crude distillation of the crude product (72.0 g) gave 50.2 g of crude product which were subsequently purified by distillation over a 20 cm Widmer column. There were obtained 47.0 g (66.1%) of pure and olfactorily good β-ionyl ethyl ether 2 of boiling point 120°-122° C./10 mmHg.

後処理

  1. customdid not exceed 50° C
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. distillationCrude distillation of the crude product (72.0 g)
  5. customgave 50.2 g of crude product which
  6. distillationwere subsequently purified by distillation over a 20 cm Widmer column

出典と根拠

ORDレコード
ord-4aadb3bff7c24f07a3de8717809ccc14
出典データセット
uspto-grants-1984_07
特許番号
US04461309

反応ノート

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