2-Methylenetetralin-1-one → 2-Methyl-1-naphthol

HRID 1198010Notes

Reaction equation

HRID 1198010 reaction equation
[H][H].[CH2:3]=[C:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14]>C1(C)C=CC=CC=1.[Pd]>[CH3:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[OH:14]

Participants

5

Reactant 2

HCID 3777512-Methylenetetralin-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 240552-Methyl-1-naphtholYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

A 50-ml reaction vessel was charged with 20 ml of toluene and 100 mg of 5% Pd/C (dry type) and hydrogen gas was passed through the mixture at room temperature. After conducting activation for 1 hour, the atmosphere in the vessel was replaced with nitrogen and the vessel was heated to 110° C. To the mixture a solution of 1.25 g (7.9 mmoles) of 2-methylene-1-tetralone in 20 ml of toluene was added dropwise over 2 hours. After the addition, refluxing state was maintained for further 1 hour to permit the reaction to proceed until completion. GLC analysis revealed that there was formed 1.23 g of 2-methyl-1-naphthol (conversion: 98.5%; selectivity: 100%).

Workup

  1. customA 50-ml reaction vessel
  2. customwas passed through the mixture at room temperature
  3. customfor 1 hour
  4. additionAfter the addition
  5. temperaturerefluxing state
  6. temperaturewas maintained for further 1 hour
  7. customthe reaction

Sources & evidence

ORD record
ord-1269fa18f9b84ae3a0987d42e625c6c0
Source dataset
uspto-grants-1994_01
Patent number
US05278343

Reaction notes

Loading…