2-Indanol → Octahydro-1H-inden-2-ol

HRID 2371759Notes

Reaction equation

HRID 2371759 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[OH:10]>CO.[Rh]>[CH2:1]1[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH:2]1[OH:10]

Participants

4

Reactant 1

HCID 779362-Indanol

Product 1

HCID 12537367Octahydro-1H-inden-2-ol

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 13.4 g (10.0 mmol) of 2-indanol in 100 mL of dry methanol was added 3.0 g of 5% Rh on carbon under a stream of argon. The solution was shaken in a Parr hydrogenation apparatus under hydrogen at 60 psi and 20° C. for 8 h. The mixture was filtered through Celite 545, rinsing with methanol, and the filtrate concentrated and distilled to give 4.2 g (30%) of (2 alpha and 2 beta 3a alpha, 7a alpha)-octahydro-1H-inden-2-ol, bp 130°-131° C. (18 mm); TLC Rf 0.68, 0.60 (SiO2, ethyl ether, molybdophosphoric acid-dark blue).

Workup

  1. filtrationThe mixture was filtered through Celite 545
  2. washrinsing with methanol
  3. concentrationthe filtrate concentrated
  4. distillationdistilled

Sources & evidence

ORD record
ord-015bdb1ec98244fb8e4aa9708f509560
Source dataset
uspto-grants-1992_03
Patent number
US05095109

Reaction notes

Loading…