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

HRID 842342Notes

Reaction equation

HRID 842342 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>CC(O)C>[CH2:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@H:1]([OH:11])[CH2:2]1

Participants

3

Reactant 1

HCID 107241-Tetralone

Product 1

HCID 7058028(R)-(-)-1,2,3,4-Tetrahydro-1-naphtholYield 96.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Tetralone (200 ml, 1.5 mol) was charged to the catalyst solution, followed by 2-propanol (0.5 l). The pressure was reduced (28.5 mmHg) and then a sodium 2-propoxide solution (120 ml of 0.1M solution in 2-propanol) was charged. The mixture was stirred at ambient temperature under nitrogen for 4.5 h, at hourly intervals 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 96.9%, ee 86.9%. The turnover number, integrated over 1 h, was 358 h−1.

Workup

  1. additioncharged
  2. customremoved by distillation

Sources & evidence

ORD record
ord-c356c48258fd4ea2ba6c0dd4f8955d41
Source dataset
uspto-grants-2002_04
Patent number
US06372931B1

Reaction notes

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