Dichloromethane → 9-Tetradecen-1-ol, acetate

HRID 638393

반응식

HRID 638393 반응식
[CH:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:16]([OH:30])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH2:26][CH2:27][CH2:28][CH3:29].ClCCl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>CCCCCC>[CH:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:1]([O:30][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:15])[CH3:2]

참가 물질

7

반응물 4

HCID 6344Dichloromethane2회HCID 37064Tetradec-9-en-1-olHCID 620729-TetradecenalHCID 178418287HCID 178418287, 화합물

생성물 2

HCID 280169-Tetradecen-1-ol, acetate수율 36%HCID 620729-Tetradecenal

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

A 2/1 trans to cis ratio of 9-tetradecenal was evaluated in the same manner as was used in the preceding example. The 9-tetradecenal was prepared from 9-tetradecenyl alcohol prepared in the same manner as described in the preceding example. About 21 grams of the alcohol in a 50/50 weight ratio selection of dichloromethane was added dropwise to a flask charged with 43 g (0.2 mol) pyridinium chlorochromate, 20 g celite and 200 mL dichloromethane. The mixture was stirred at room temperature for about 2 hours after addition of the alcohol solution was complete. Then 200 mL of hexane was added and the mixture was filtered. The solvent was evaporated and the product vacuum distilled through a 2 ft.×3/4 in. packed column (Penn State stainless steel packing). A 36% yield of pure 9-tetradecenyl acetate was obtained.

후처리

  1. customprepared in the same manner
  2. filtrationthe mixture was filtered
  3. customThe solvent was evaporated
  4. distillationthe product vacuum distilled through a 2 ft.×3/4 in

출처 및 근거

ORD 기록
ord-15213315cdd642e3beb096e340f51c27
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560792

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