tert-Butanol → 3-Tert-butyl-5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthol

HRID 1790998Notes

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.[C:22](O)([CH3:25])([CH3:24])[CH3:23].FC(F)(F)S(O)(=O)=O>ClC1C=CC=CC=1Cl.O.CCOCC>[C:22]([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)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol (1.0 g, 3.4 mmol), tert-butyl alcohol (1.4 g), trifluoromethanesulfonic acid (0.04 g) was dissolved in 2 ml 1,2-dichlorobenzene. The mixture was heated at 120° C. for 2.5 hours. GC showed 97% conversion to 87% mono-butylated product, and 10% bis-butylated product. The mixture was cooled, and diluted with 10 ml water and 10 ml ether. The layers were separated, and the organic layer was washed with sodium bicarbonate solution, dried, and concentrated. The crude product was purified by flash column chromatography (silica gel, 2% ethyl acetate/hexanes) to yield 0.7 g of white solid.

Workup

temperatureThe mixture was cooled
customThe layers were separated
washthe organic layer was washed with sodium bicarbonate solution
customdried
concentrationconcentrated
customThe crude product was purified by flash column chromatography (silica gel, 2% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-71922025b2c742d789cbad502858e85d
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071365B2

Reaction notes

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