1-Tetralone → 1,2,3,4-Tetrahydro-1-naphthalenol

HRID 1855141Notes

Reaction equation

HRID 1855141 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>C(O)C>[CH:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 107241-TetraloneHCID 14797Potassium Hydroxide

Product 1

HCID 107231,2,3,4-Tetrahydro-1-naphthalenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
80 °C

Procedure

Tris(triphenylphosphine)ruthenium (II) chloride (1.9 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=i-Pr, Ar=C6H5—, 1.3 μmol, 0.33 mol %) were dissolved in ethanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 80° C. After the mixture was cooled to room temperature, 1-tetralone (0.4 mmol), ethanol (2 mL) and a solution of potassium hydroxide in ethanol (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 48 h under H2 (10 atm) at 0° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5). Accordingly, pure 1,2,3,4-tetrahydro-1-naphthol was obtained and the ee value (ee=99.7%) was measured by GC analysis.

Workup

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 48 h under H2 (10 atm) at 0° C
  4. customThe solvent was removed under reduced pressure
  5. customthe resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5)

Sources & evidence

ORD record
ord-373dc332e7d94c2c8956c3d069d290c4
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

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