Dimethyl Sulfoxide → 11-Hexadecenal, (11Z)-

HRID 1380166

반응식

HRID 1380166 반응식
[CH:1](Br)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CS(C)=[O:20].C([O-])(O)=O.[Na+]>>[CH:1](=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH3:16]

참가 물질

4

반응물 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 54030172Hexadecenyl bromide

생성물 1

HCID 536449511-Hexadecenal, (11Z)-수율 38%

반응 조건

온도
60 °C

실험 절차

Run 3 (invention): The oxidation procedure employed for run 2 was repeated on a larger scale. Thus, 360 g (1.2 mol) of hexadecenyl bromide and 1800 mL (1980 g; 25.4 mol) of DMSO were mixed and heated to 60° C., with temperature maintained at 60° C. for about 30 minutes. Then, 240 g (2.9 mol) of NaHCO3 was added and the temperature of the reaction mixture raised to 130° C., which was maintained for 2 hours. The reaction mixture was then cooled and filtered. The lower layer (DMSO layer) was separated and extracted with about 1 L of hexane. The hexane extract and upper (aldehyde) layer were combined, washed once with about 100 mL of water, then concentrated on a rotary evaporator. GLC analysis indicated an aldehyde/alcohol ratio of 4.5:1. A distilled yield of 38% Z-11-hexadecenal was obtained.

후처리

  1. temperaturemaintained at 60° C. for about 30 minutes
  2. temperaturethe temperature of the reaction mixture raised to 130° C.
  3. temperaturewhich was maintained for 2 hours
  4. temperatureThe reaction mixture was then cooled
  5. filtrationfiltered
  6. customThe lower layer (DMSO layer) was separated
  7. extractionextracted with about 1 L of hexane
  8. extractionThe hexane extract
  9. washwashed once with about 100 mL of water
  10. concentrationconcentrated on a rotary evaporator

출처 및 근거

ORD 기록
ord-cfe6c5d543df4f57a0a88a22458461b5
출처 데이터셋
uspto-grants-1986_04
특허 번호
US04579977

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