1,4-Dichlorobenzene → 3,3'-Diisopropyl-5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthol

HRID 1790995

Reaction equation

[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].[CH:25]1[C:30](Cl)=CC=C(Cl)[CH:26]=1>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]>[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[C:20]([CH:25]([CH3:30])[CH3:26])=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:24])[CH3:22]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol (44.0 g), dichlorobenzene (10 ml) and phosphotungstic acid (2.3 g) was heated to 130° C. To the mixture was added excess propylene via a dry-ice condenser. The reaction was monitored by GC analysis. The reaction mixture contained 6% of monoisopropylated product and 83% of diisopropylated product. The mixture was purified by flash column to give 20.0 g of 3,3′-diisopropyl-5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol.

Workup

customThe mixture was purified by flash column

Sources & evidence

ORD record: ord-366fafc4eb344e6ebc2c03201dcde3fe
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071365B2

Linked notes

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