1-Tetralone → (R)-(-)-1,2,3,4-Tetrahydro-1-naphthol

HRID 842339Notes

Reaction equation

HRID 842339 reaction equation
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1>CC(O)C>[CH2:1]1[CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C@H:9]([OH:10])[CH2:11]1

Participants

3

Reactant 1

HCID 107241-Tetralone

Product 1

HCID 7058028(R)-(-)-1,2,3,4-Tetrahydro-1-naphtholYield 98.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
35 °C

Procedure

Sodium 2-propoxide (0.38 ml of 0.1M solution in 2-propanol) was charged to the catalyst solution followed by the α-tetralone (0.5 ml, 3.76 mmol). The mixture was stirred under vacuum (80 mmHg) at 35° C. for 2 h, after the first hour the flask was back filled with nitrogen and sufficient 2-propanol charged to compensate for the volume removed by distillation. This gave (R)-1-tetralol Yield 98.4%, ee 95.7%. The turnover number, integrated over 1 h, was 185 h−1.

Workup

  1. additioncharged
  2. customremoved by distillation

Sources & evidence

ORD record
ord-6f1ea6cdcbc54d7fa1977c13f138e5c8
Source dataset
uspto-grants-2002_04
Patent number
US06372931B1

Reaction notes

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