Propylene → 3-Isopropyl-5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthol

HRID 1790994

반응식

HRID 1790994 반응식
[C:1]1([OH:21])[C:2]([C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:12]=2)=[CH:3][CH:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2.[CH2:22]=[CH:23][CH3:24]>O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.P.[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].[W].C1(C)C(C)=CC=CC=1>[CH:23]([C:3]1[CH:4]=[C:5]2[C:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)=[C:1]([OH:21])[C:2]=1[C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:24])[CH3:22]

참가 물질

5

반응물 2

HCID 8252PropyleneHCID 220441995,5',6,6',7,7',8,8'-Octahydro-2,2'-binaphthol2회

생성물 1

HCID 220441953-Isopropyl-5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthol수율 42%

시약·촉매·용매 2

HCID 45231312-Wolframophosphoric acid촉매HCID 7237O-Xylene용매

반응 조건

온도
140 °C

실험 절차

A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol (30.0 g), xylene (5 ml) and phosphotungstic acid (1.5 g) was heated to 140° C. To the mixture was added propylene (8.9 g) slowly via a dry-ice condenser. GC analysis of the reaction mixture indicated that 98% conversion of the 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol. Small amounts of isopropylated xylene were observed as well. The mixture was purified by flash column to give 14.5 g of 3-isopropyl-5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol, mp 110° C.; 3.7 g of 3,3′-diisopropyl-5,5′,6,6′,7,7′8,8′-octahydro-2,2′-binaphthol, mp 152–3° C.; and a mixture (15 g) containing 38% of 3-isopropyl-5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol and 33% of 3,3′-diisopropyl-5,5′,6,6′,7,7′8,8′-octahydro-2,2′-binaphthol.

후처리

  1. customThe mixture was purified by flash column

출처 및 근거

ORD 기록
ord-fecd8c4325a044fe9432bcdb6bfcaf63
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071365B2

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