6-Octenal, 3,7-dimethyl-, (3R)- → (3r)-3,7-Dimethyloctanal

HRID 414139

반응식

HRID 414139 반응식
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@H:7]([CH2:9][CH:10]=[O:11])[CH3:8])[CH3:3]>C(OCC)(=O)C.[Pt]=O>[CH3:8][C@H:7]([CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])[CH2:9][CH:10]=[O:11]

참가 물질

4

반응물 1

HCID 754276-Octenal, 3,7-dimethyl-, (3R)-2회

생성물 1

HCID 12266719(3r)-3,7-Dimethyloctanal

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매2회HCID 8857Ethyl Acetate용매

실험 절차

A 3 L indented flask equipped with a mechanical stirrer and a H2 inlet was charged with 205.7 g (1.333 mol) of (R)-citronellal in 7.4 L of ethyl acetate. The flask was flushed with 0.1 cu. ft. of H2 and 0.50 g (2.0 mmol) of platinum oxide were added. The reaction was stirred under a slight over-pressure of H2 at ambient temperature for 124 hours. During this time, due to relatively rapid deactivation of the catalyst, an additional 3.50 g (143. mmol) of platinum oxide had to be added in 5 portions (0.5 g at 3.5 hours., 0.5 g at 22.5 hours., 1.0 g at 96.5 hours and 0.5 g at 121 hours). The course of the hydrogenation was monitored by GC analysis. After 124 hours, GC indicated the hydrogenation to be almost complete with 1.4% of starting material remaining. A total of 1.133 cu. ft. of hydrogen (theoretically 1.166 cu. ft.) had been consumed. The catalyst was removed by filtration through a pad of Celite (diatomeaceous earth). The clear filtrate was combined with the filtrate from a previously run, analogous reduction of 10.0 g (64.8 mmol) of (R)-citronellal and concentrated on the rotovapor. Vacuum distillation of the obtained pale yellow liquid through a 30 cm Goodloe column afforded the (R)-3,7-dimethyloctanal in following fractions:

후처리

  1. customequipped with a mechanical stirrer and a H2 inlet
  2. additionwere added
  3. additionto be added in 5 portions (0.5 g at 3.5 hours., 0.5 g at 22.5 hours., 1.0 g at 96.5 hours and 0.5 g at 121 hours)
  4. waitAfter 124 hours
  5. customA total of 1.133 cu. ft. of hydrogen (theoretically 1.166 cu. ft.) had been consumed
  6. customThe catalyst was removed by filtration through a pad of Celite (diatomeaceous earth)
  7. distillationVacuum distillation of the obtained pale yellow liquid through a 30 cm Goodloe column

출처 및 근거

ORD 기록
ord-4ff402c7888d44fe913570785a9d0582
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04789750

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