1-Naphthol → 1-(1-Naphthyl)-2-naphthol
Reaction equation
[C:1](N)(=O)[C@H:2]([C@@H:4]([C:6](N)=[O:7])O)O.[C:11]1(O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1>>[C:14]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[C:6]([OH:7])=[CH:4][CH:2]=[C:1]2[C:13]=1[CH:12]=[CH:11][CH:20]=[CH:19]2Participants
Procedure
On the other hand, 2.7 g of (+)-binaphthol (VII) ([α]D20, +21.0° (C=0.55, tetrahydrofuran)) which was obtained by silica gel chromatography of the filtrate obtained when the clathrate compound was separated and 2.19 g of (-)-(S,S)-tartaric acid diamide (X) were dissolved in the above-described mixed solvent, and thus-obtained solution was allowed to stand for 12 hours at room temperature. The crystallized crystal was recrystallized once to obtain 2.70 g of a clathrate compound (colorless prismatic crystal: mp, 150-151° C.; [α]D20, -43.9° (CHCl3)) containing (-)-tartaric acid diamide (X) and (+)-naphthol (XI) in a ratio of 1 : 1. The obtained crystal was subjected to column chromatography to obtain 1.48 g of (+)-binaphthol (VII) ([α]D20, +36.5° (C=1.3, tetrahydrofuran)).
Sources & evidence
- ORD record
- ord-00dd28976e034ebbae195f643b4b9cce
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05306844
Reaction notes
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