1-Hexene → Dec-5-enyl acetate

HRID 323917

반응식

HRID 323917 반응식
[C:1]([OH:12])(=O)[CH2:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:13]([O-])(=[O:23])[CH2:14]CCC=CCCCC.C=CCCCC>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[C:13]([O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:23])[CH3:14]

참가 물질

5

반응물 3

HCID 115971-HexeneHCID 534008795-Decenoic acidHCID 740529265-Decenoate

생성물 1

HCID 38027Dec-5-enyl acetate

시약·촉매·용매 1

HCID 178479819HCID 178479819, 화합물촉매

실험 절차

For example, 5-hexenoic acid or an ester of 5-hexenoic acid (e.g. methyl 5-hexenoate, ethyl 5-hexenoate, etc.) could be used instead of 1-hexene, but the synthesis would entail a reduction of a carboxylic acid or an ester to an alcohol followed by acetylation. These syntheses are respectively shown in FIGS. 6 and 7. With reference to FIGS. 6 an 7, the 5-hexenoic acid or 5-hexenoate is reacted with 5-decene to form 5-decenoic acid or 5-decenoate, respectively, in the presence of Grubbs' catalyst and under vacuum. The resulting 5-decenoic acid or 5-decenoate are then reacted with 1-hexene, reduced, and acetylated to form 5-decenyl acetate. In addition, synthesizing 5-decenoic acid would have advantages because the salt of 5-decenoic acid could be recrystallized to increase the trans-isomer to greater than 90 percent trans-5-decenoic acid, which is then reduced and acetylated to greater than 90 percent trans-5-decenyl acetate.

출처 및 근거

ORD 기록
ord-17541b9e0cb14cc4b24e28175de70a86
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06215019B1

연결된 노트

불러오는 중…