Hydrochloric Acid → 9-Octylheptadecan-9-ol

HRID 2587

Reaction equation

HRID 2587 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Mg].C(=O)([O:15][CH2:16][CH3:17])OCC.Cl>C(OCC)C>[CH2:1]([C:16]([CH2:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 81401-BromooctaneHCID 5462224Magnesium

Product 1

HCID 872399-Octylheptadecan-9-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
30 °C

Procedure

This compound may be prepared in the following manner. Three moles of n-octylbromide are slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether is slowly added to the mixture. The mixture is stirred for one hour at 30° C., then the mixture is slowly poured into 1.8 liters of a cold 10% HCl solution. The organic layer is dried with magnesium sulfate and the ethyl ether is evaporated off to give tri-n-octylcarbinol.

Workup

  1. customThis compound may be prepared in the following manner
  2. dry with materialThe organic layer is dried with magnesium sulfate
  3. customthe ethyl ether is evaporated off

Sources & evidence

ORD record
ord-53f58a0bd1b3472b91143912053c2870
Source dataset
uspto-grants-1998_03
Patent number
US05728907

Linked notes

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