Iodine → p-(1-Cyclooctenyl)-anisol

HRID 1764128

反応式

HRID 1764128 の反応式
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[C:13]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl-].[NH4+]>O1CCCC1.C(Cl)(Cl)Cl>[C:13]1([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1

参加物

8

反応物 5

HCID 807IodineHCID 77304-BromoanisoleHCID 10403CyclooctanoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

生成物 1

HCID 284297p-(1-Cyclooctenyl)-anisol

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
15 °C

実験手順

To a vigorously stirred suspension of 19.5 g of magnesium chips (which have been washed with chloroform and activated with iodine) in 800 ml of absolute tetrahydrofuran is added in increments a solution of 131 g of p-bromanisol in 200 ml of absolute tetrahydrofuran in such a way that it is possible to maintain gently the Crignard reaction. The reaction mixture is allowed to continue to react for 1 hour, cooled to 15° C and treated dropwise with 88 g of cyclooctanone. After the reaction mixture has been stirred for a further 5 hours, it is treated with ice and with saturated ammonium chloride solution. The whole mixture is extracted with ether, the ether layers are washed with water, dried over sodium sulphate and evaporated in vacuo. During distillation under a high vacuum, water is split off from the oily residue to thus yield the p-(1-cyclooctenyl)-anisol, which boils at 115°-118° C (0.05mm Hg).

後処理

  1. temperatureto maintain gently
  2. customthe Crignard reaction
  3. customto react for 1 hour
  4. extractionThe whole mixture is extracted with ether
  5. washthe ether layers are washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo
  8. distillationDuring distillation under a high vacuum, water
  9. customis split off from the oily residue

出典と根拠

ORDレコード
ord-f7f504eabccd417f923fc3a2b0b66506
出典データセット
uspto-grants-1978_09
特許番号
US04115416

関連ノート

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