Hydrochloric Acid → Binol

HRID 1021013Notes

Reaction equation

HRID 1021013 reaction equation
[C:1]1([C@@H:7](NC[C@H](CCC)CC(O)=O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:22][CH2:23][CH3:24])(=O)C.Cl>CO>[CH:1]1[CH:6]=[C:5]2[CH:4]=[CH:24][C:23]([OH:22])=[C:7]([C:1]3[C:2]4[C:3](=[CH:8][CH:7]=[CH:23][CH:24]=4)[CH:4]=[CH:5][C:6]=3[OH:22])[C:8]2=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 66666530HCID 66666530, compound

Product 1

HCID 11762Binol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

(R,S)-3-[(1-phenyl ethylamino)-methyl]-hexanoic acid (5.0 g) is dissolved in methanol (20 mL) and (RS)-1,1′-bi-2-naphthol (5.75 g) is added to it at room temperature. The mixture is stirred at 50° C. for 1 hour, during which time solid precipitate comes out from the reaction mixture. Reaction mixture is allowed to cool to room temperature and filtered under reduced pressure to obtain 3.7 g of solid complex. Complex is suspended in the biphasic mixture of ethyl acetate (20 mL) and 1 N hydrochloric acid (20 mL) and stirred for 30 to 45 min to decompose the complex. Aqueous phase is washed with 10 mL ethyl acetate. Organic phases are mixed together and washed with brine, followed by drying over sodium sulfate. Solvent is evaporated under vacuum to obtain optically pure (5)-1,1′-bi-2-naphthol (1.56 g) having 95% ee.

Workup

  1. customReaction mixture
  2. temperatureto cool to room temperature
  3. filtrationfiltered under reduced pressure
  4. customto obtain 3.7 g of solid complex
  5. stirringstirred for 30 to 45 min
  6. washAqueous phase is washed with 10 mL ethyl acetate
  7. additionOrganic phases are mixed together
  8. washwashed with brine
  9. dry with materialby drying over sodium sulfate
  10. customSolvent is evaporated under vacuum

Sources & evidence

ORD record
ord-9e129dcc34964bcb99125c3c3800ebca
Source dataset
uspto-grants-2014_05
Patent number
US08716520B2

Reaction notes

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