1-Bromooctane → HCID 22242474, compound

HRID 890906Notes

Reaction equation

HRID 890906 reaction equation
[OH:1][C:2]([CH3:13])([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CS(C)=O>[OH:1][C:2]([CH3:13])([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:7][CH:6]=1)=[O:4].[CH3:12][C:2]([O:1][CH2:12][CH2:2][CH2:3][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 22239681110538-16-4

Product 2

HCID 22242474HCID 22242474, compoundYield 85%HCID 22242478HCID 22242478, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
37.5 °C

Procedure

A solution of 2-hydroxy-1-(4-hydroxyphenyl)-2-methyl-1-propanone (10 g, 55.5 mmol) in dimethyl sulfoxide (DMSO) (125 ml) is added in the course of 1 hour at room temperature (RT), under argon, to a suspension of NaH (2.66 g, 61 mmol, 1.1 eq; 55–60% in oil, washed with hexane) in DMSO (40 ml). The mixture is stirred for 15 minutes at RT and for 15 minutes at from 35 to 40° C. A solution of 1-bromooctane (11.79 g, 61 mmol) in DMSO (10 ml) is added in the course of 15 minutes and the mixture is heated at 190° C. for 18 hours. The solution is poured onto ice and the resulting mixture is extracted with tert-butyl methyl ether (TBME). The organic phases are dried with MgSO4. After filtration and removal of the solvent by evaporation, the compound is obtained in the form of an oil. Flash chromatography yields 2-hydroxy-2-methyl-1-(4-octyloxy-phenyl)-propan-1-one (13.9 g, 85%) in the form of a yellow oil and 2-methyl-2-octyloxy-1-(4-octyloxy-phenyl)-propan-1-one (1.1 g; 5%) in the form of a yellow oil.

Workup

  1. temperaturethe mixture is heated at 190° C. for 18 hours
  2. additionThe solution is poured onto ice
  3. extractionthe resulting mixture is extracted with tert-butyl methyl ether (TBME)
  4. dry with materialThe organic phases are dried with MgSO4
  5. filtrationAfter filtration and removal of the solvent
  6. customby evaporation
  7. customthe compound is obtained in the form of an oil

Sources & evidence

ORD record
ord-cbb716b5b75e48069102bdc681dad49b
Source dataset
uspto-grants-2006_02
Patent number
US07001644B2

Reaction notes

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