1-Acetylnaphthalene → (1R)-1-(Naphthalen-1-yl)ethan-1-ol

HRID 1358713Notes

Reaction equation

HRID 1358713 reaction equation
[OH-].[K+].CC(O)C.[C:7]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)(=[O:9])[CH3:8].[H][H]>CC(O)C>[C:10]1([C@H:7]([OH:9])[CH3:8])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 136631-AcetylnaphthaleneHCID 23443544KOH isopropanolHCID 178418361HCID 178418361, compound

Product 1

HCID 6976567(1R)-1-(Naphthalen-1-yl)ethan-1-olYield 53%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 100 mL of an autoclave was charged 11.7 mg (0.010 mmol) of the mixture of RuCl2[(R)-binap](dmf)n and RuCl2[(S) -binap][(S)-binaphthyldiamine]. After purging with argon, 2.8 mL of 2-propanol and 50 μL (0.025 mmol) of KOH/2-propanol (0.5M solution) were added. The resulting mixture was stirred at room temperature for 30 minutes. After addition of 0.38 mL (2.5 mmol) of 1′-acetonaphthone, stirring was conducted at room temperature for 4 hours at a hydrogen pressure adjusted to 0.8 Mpa. The reaction mixture was concentrated by distilling off the solvent under reduced pressure. The residue was filtered using silica gel, whereby 228 mg (yield: 53%) of (R)-1-(1-naphthyl)ethanol was obtained. The enantio-selectivity was 4%ee.

Workup

  1. additionwere added
  2. stirringstirring
  3. concentrationThe reaction mixture was concentrated
  4. distillationby distilling off the solvent under reduced pressure
  5. filtrationThe residue was filtered

Sources & evidence

ORD record
ord-e83cd616ba9c4c629b2dfd6d636474d8
Source dataset
uspto-grants-2003_07
Patent number
US06596887B2

Reaction notes

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