Iodine → p-(1-Cyclooctenyl)-anisol

HRID 1764128

반응식

HRID 1764128 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

HCID 284297p-(1-Cyclooctenyl)-anisol

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
15 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f7f504eabccd417f923fc3a2b0b66506
출처 데이터셋
uspto-grants-1978_09
특허 번호
US04115416

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