Water → (E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate

HRID 922000

반응식

HRID 922000 반응식
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10][OH:11])/[CH3:8])[CH3:3].N1C=CC=CC=1.[Cl:18][CH2:19][C:20](Cl)=[O:21].O>ClCCl>[Cl:18][CH2:19][C:20]([O:11][CH2:10]/[CH:9]=[C:7](\[CH3:8])/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])=[O:21]

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 637566Geraniol

생성물 1

HCID 5890636(E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Geraniol [1] (7.711 g, 50 mmol) and pyridine (3.955 g, 50 mmol) were suspended in anhydrous dichloromethane (200 ml) and chilled to 0° C. under an atmosphere of dry nitrogen. Chloroacetylchloride (5.647 g, 50 mmol) was added dropwise (violent reaction) and the resulting solution was stirred for 24 hrs at room temperature. Water (100 ml) was added, the organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic layers were successively washed with 2N HCl, saturated NaHCO3 solution and brine, dried over MgSO4 and the solvent was evaporated. Remaining volatile material was removed under reduced pressure (0.01 mbar) to yield product [2] as yellow liquid. The product was pure according to 1H NMR and directly subjected to the next step without further purification.

후처리

  1. custom(violent reaction)
  2. customthe organic layer was separated
  3. extractionthe aqueous layer extracted with dichloromethane
  4. washThe combined organic layers were successively washed with 2N HCl, saturated NaHCO3 solution and brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was evaporated
  7. customwas removed under reduced pressure (0.01 mbar)

출처 및 근거

ORD 기록
ord-22a5ea835527400ca78cd04294bdb569
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278134B2

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