1-Acetylnaphthalene → 2-Naphthalen-1-ylpropan-2-ol

HRID 618756Notes

Reaction equation

HRID 618756 reaction equation
[CH3:1][C:2]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=[O:3].[CH3:14][Li]>C(OCC)C>[OH:3][C:2]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)([CH3:14])[CH3:1]

Participants

4

Reactant 2

HCID 136631-AcetylnaphthaleneHCID 178418348HCID 178418348, compound2×

Product 1

HCID 2381992-Naphthalen-1-ylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 10 ml (65.8 mmole) quantity of 1-acetonaphthone was dissolved in 150 ml of diethyl ether in a 500 ml, two neck, round bottom flask equipped with a pressure equalizing dropping finnel and fitted with a rubber septum and a protected reflux condenser. A 138 ml (98 mmole) quantity of 1.4 M methyllithium in ether (Aldrich) was transferred to the fiumel by use of a cannula and nitrogen pressure. This was slowly added to the stirred ketone over a 20 minute period. A light green color indicated an excess of methyllithium. This was refluxed for an additional hour and the reaction was carefully quenched with water. The ether layer was made acidic using HCl, neutralized with NaHCO3, dried using MgSO4, and filtered. After the solvent was removed, the crude product was recrystallized from benzene, filtered and washed with cold pentane to yield white, fibrous crystals (>98%), m.p. 81-86° C. 1H NMR (acetone-d6): (=9.01 (m, 1 H, aromatic), 7.95 (m, 1 H, aromatic), 7.82 (d, J=10.6, 1 H, aromatic), 7.68 (d, J=10.3, 1 H, aromatic), 7.50 (m, 3 H, aromatic), 4.30 (s, 1 H, --OH), 1.84 (s, 6 H, --CH3).

Workup

  1. customequipped with a pressure
  2. customfitted with a rubber septum and a protected reflux condenser
  3. temperatureThis was refluxed for an additional hour
  4. customthe reaction was carefully quenched with water
  5. customdried
  6. filtrationfiltered
  7. customAfter the solvent was removed
  8. customthe crude product was recrystallized from benzene
  9. filtrationfiltered
  10. washwashed with cold pentane
  11. customto yield white

Sources & evidence

ORD record
ord-562930c875894369a255b8152e003015
Source dataset
uspto-grants-1999_09
Patent number
US05955509

Reaction notes

Loading…