Hydrochloric Acid → Binol

HRID 1608718Notes

Reaction equation

HRID 1608718 reaction equation
CO.Cl.[CH:4]1[CH:9]=[C:8]2[CH:10]=[CH:11][C:12]([OH:25])=[C:13]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][C:15]=3[OH:24])[C:7]2=[CH:6][CH:5]=1.[C@@H]1(N)CCCC[C@H]1N>C1C=CC=CC=1>[CH:20]1[CH:19]=[C:18]2[CH:17]=[CH:16][C:15]([OH:24])=[C:14]([C:13]3[C:7]4[C:8](=[CH:9][CH:4]=[CH:5][CH:6]=4)[CH:10]=[CH:11][C:12]=3[OH:25])[C:23]2=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11143843HCID 11143843, compound

Product 1

HCID 11762BinolYield 98.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5 ml of methanol and. 50 ml of 0.1M hydrochloric acid were added under ice cooling to 2.55 g (4.58 mmol) of (R)-(+)-2,2'-dihydroxy-1,1'-binaphthyl-(1R,2R)-(-)1,2-cyclohexanediamine.benzene (1:1:2) complex obtained in the same manner as in Example 5, followed by stirring for 30 minutes. The precipitated white solid was washed with water, and then dried under reduced pressure to obtain 1.29 g (4.51 mmol) of (R)-(+)-2,2'-dihydroxy-1,1'-binaphthyl. Yield =98%, optical purity=81%, m.p.=202°-203° C., and [α]D24 =+29.7° (c 0.539, THF).

Workup

  1. washThe precipitated white solid was washed with water
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-8b930a57b6364169b38275f0bc9a79de
Source dataset
uspto-grants-1995_03
Patent number
US05395962

Reaction notes

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