ChemicalBook CAS DataBase List R-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol

R-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol synthesis

4synthesis methods

Product Name:R-3,3'-Bis(phenyl)-1,1'-bi-2-naphthol
CAS Number:75684-93-4
Molecular formula:C32H22O2
Molecular Weight:438.52

75714-59-9 Synthesis

(R)-3,3'-DIBROMO-2,2'-DIMETHOXY-1,1'-BINAPHTHYL

75714-59-9
76 suppliers
$45.00/2.5mg

100-58-3
185 suppliers
$18.00/10ml

75684-93-4
41 suppliers
$69.00/100mg

Yield: 63%

Reaction Conditions:

Stage #1:(Ra)-3,3’-dibromo-2,2’-dimethoxy-1,1’-binaphthalene;bis(triphenylphosphine)nickel(II) chloride in diethyl ether for 0.333333 h;
Stage #2:phenylmagnesium bromide in diethyl ether for 20 h;Heating / reflux;
Stage #3: with boron tribromide in dichloromethane at 0 - 25;

Steps:

11 Example 11; Preparation of (R)-3,3'-Diphenyl-2,2'-dihydroxy-1,1'-dinaphthyl
To a suspension of 7.7 g (16.3 mmol) of (R)-3,3'-dibromo-2,2'-dimethoxy-1,1'-dinaphthyl and 0.6 g (0.92 mmole) of dichlorobis (triphenylphosphine) nickel (II) in 100 ml of ether stirred under nitrogen was added (after 20 minutes) a solution of 45 mmol of phenylmagnesium bromide in 60 ml of ether. The mixture was refluxed for 20 hours, cooled, and shaken with 600 ml each of chloroform and 1 M hydrochloric acid. The organic layer was dried, evaporated, and dissolved in 50 ml of hot benzene and then chromatographed as 300 g of silica gel suspended in benzene. The combined fractions (7 g) were dissolved in 600 ml of methylene chloride and cooled to 0° C. About 26 g (96 mol) of tribromoborane was then added. After being stirred for 26 hours at 25° C., the mixture was cooled to 0° C. and the excess of tribromoborane was decomposed by dropwise addition of water. The mixture was shaken with 300 ml of water and the organic layer was dried, concentrated to 30 ml, and chromatographed in 300 g of silica. Washing the column with benzene-ethyl ether gave 4.4 g (63% overall) of (R)-3,3'-diphenyl-2,2'-dihydroxy-1,1'-dinaphthyl. The compound was recrystalized from methylene chloride-cyclohexane m.p. 197°-198° C. ¹HNMR(δ), 5.48(s,2H), 7.6 (m.20H).

References:

IBC Advanced Technologies, Inc. US6686479, 2004, B2 Location in patent:Page column 14

30889-48-6 Synthesis