1-Octene → 6-Octyl-3,4-dihydronaphthalen-2(1H)-one

HRID 507496Notes

Reaction equation

HRID 507496 reaction equation
B([O-])O[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C=CCCCCCC.B1C2CCCC1CCC2.[OH-].[Na+].Br[C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[CH2:38][C:37](=[O:42])[CH2:36][CH2:35]2>C1COCC1>[CH2:3]([C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[CH2:38][C:37](=[O:42])[CH2:36][CH2:35]2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 5

HCID 81251-OcteneHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 27335536-Bromo-2-tetraloneHCID 178443689HCID 178443689, compound

Product 1

HCID 685939856-Octyl-3,4-dihydronaphthalen-2(1H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An octyl boronate intermediate is first generated by adding 1-octene (1.38 g, 14.1 mmol) to a solution of 9-BBN in THF (28.3 mL of a 0.5 M solution, 14.1 mmol). The reaction is stirred at room temperature overnight, then an aqueous solution of sodium hydroxide (5.0 mL of a 3.0 M solution) is added, followed by the addition of 6-bromo-2-tetralone (2.40 g, 10.0 mmol) and Pd[P(Ph)3]4 (0.310 g, 0.270 mmol). The reaction is brought to reflux and maintained for 12 hours under an inert atmosphere. The reaction is then cooled, filtered, concentrated in vacuo and the residue purified using silica gel chromatography with hexanes/ethyl acetate (75:25) as solvent to provide 6-octyl-2-tetralone (2.35 g, 8.5 mmol, 85%) as a clear liquid.

Workup

  1. temperatureto reflux
  2. temperaturemaintained for 12 hours under an inert atmosphere
  3. temperatureThe reaction is then cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe residue purified

Sources & evidence

ORD record
ord-c44a5af797b2413197d97604c7fe7ac0
Source dataset
uspto-grants-2010_08
Patent number
US07786173B2

Reaction notes

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