Chloroform → HCID 54386604, 화합물

HRID 1196172

반응식

HRID 1196172 반응식
[CH3:1][C:2]([CH3:11])=[CH:3][CH2:4][CH2:5][C:6]([OH:10])([C:8]#[CH:9])[CH3:7].[OH-].[Na+].[CH:14]([Cl:17])(Cl)[Cl:15]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:15][C:14]1([Cl:17])[C:2]([CH3:1])([CH3:11])[CH:3]1[CH2:4][CH2:5][C:6]([CH3:7])([OH:10])[C:8]#[CH:9]

참가 물질

5

반응물 3

HCID 6212Chloroform2회HCID 14798Sodium Hydroxide2회HCID 62842Dehydrolinalool

생성물 1

HCID 54386604HCID 54386604, 화합물수율 97%

시약·촉매·용매 1

HCID 66133Benzyl triethylammonium chloride촉매2회

실험 절차

Dehydrolinalool (400 g, 2.6 mol) and 5.26 g of triethylbenzylammonium chloride are added to a reaction flask. Chloroform (469.6 g, 3.9 mol) is added dropwise. To this solution 223.2 g (2.79 mol) of 50% sodium hydroxide solution are added dropwise within 50 minutes while cooling with ice, whereby the temperature of the reaction mixture rises to 34°. In time the initially viscous mass becomes fluid. After 21 hours of stirring and then again after 37 hours, there are added in each case within 20 minutes while cooling with ice, 160 ml of chloroform, 2.63 g of triethylbenzylammonium chloride and 111.6 g of 50% NaOH. The mixture is stirred at room temperature for a further 60 hours, poured onto ice-water, extracted with methylene chloride, washed neutral, dried over magnesium sulphate and evaporated. In this manner there are obtained 603.7 g (97%) of 5-(2',2'-dichloro-3'3'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol.

후처리

  1. temperaturewhile cooling with ice, whereby the temperature of the reaction mixture
  2. customrises to 34°
  3. waitagain after 37 hours
  4. additionthere are added in each case within 20 minutes
  5. stirringThe mixture is stirred at room temperature for a further 60 hours
  6. additionpoured onto ice-water
  7. extractionextracted with methylene chloride
  8. washwashed neutral
  9. dry with materialdried over magnesium sulphate
  10. customevaporated

출처 및 근거

ORD 기록
ord-88291aa346b440e5b83b5925d1fc6679
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05113021

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