Hexanal → HCID 21273100, compound

HRID 1382697Notes

Reaction equation

HRID 1382697 reaction equation
[CH2:1]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Mg].[CH:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[Cl-].[NH4+]>O1CCCC1.C(Cl)(Cl)(Cl)Cl>[CH2:1]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 6184HexanalHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 21924050HCID 21924050, compound2×

Product 1

HCID 21273100HCID 21273100, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-70 °C

Procedure

A third of a solution of 11 g of 2-nonylbromobenzene [cf. EP-OL 0 123 543] in 15 ml of tetrahydrofuran is added to a mixture, stirred under an argon atmosphere, of 1.1 g of magnesium turnings, 8 ml of tetrahydrofuran and 3 drops of carbon tetrachloride, and the whole is heated at the boil, under reflux, for 30 minutes. The remainder of the solution of 2-nonylbromobenzene (cf. EP-OL 0 123 543) is then added dropwise over a period of 35 minutes and the reaction mixture is maintained under reflux for 2 hours. After dilution with 15 ml of tetrahydrofuran, the suspension is cooled to -10° C. and added in portions to a solution, cooled to -70° C., of 4.6 g of hexanal in 12 ml of tetrahydrofuran. After stirring for 1 hour at -70° C., 200 ml of saturated aqueous ammonium chloride solution are added to the reaction mixture, the organic layer is separated off and the aqueous layer is extracted three times with ether. The residue that remains after the combined ethereal extracts have been dried and concentrated by evaporation is purified by chromatography on silica gel with mixtures of petroleum ether with an increasing amount of methylene chloride, yielding the desired 1-(2-nonylphenyl)-1-hexanol in the form of a colourless oil.

Workup

  1. temperaturethe whole is heated at the boil
  2. temperatureunder reflux, for 30 minutes
  3. temperaturethe reaction mixture is maintained
  4. temperatureunder reflux for 2 hours
  5. additionadded in portions to a solution
  6. customthe organic layer is separated off
  7. extractionthe aqueous layer is extracted three times with ether
  8. customhave been dried
  9. concentrationconcentrated by evaporation
  10. customis purified by chromatography on silica gel with mixtures of petroleum ether with an increasing amount of methylene chloride

Sources & evidence

ORD record
ord-25c710843b4f437eb053e9e67b01e5e3
Source dataset
uspto-grants-1989_02
Patent number
US04808572

Reaction notes

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