Isopropanol → Octane

HRID 2049514Notes

Reaction equation

HRID 2049514 reaction equation
[Ni:1].CO.[C:4]([CH:8]1[C:15](C(C)(C)C)(O)[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9]1)(C)(C)[CH3:5].CC(O)C>C1C=CC=CC=1>[Ni:1].[CH3:11][OH:12].[CH3:5][CH2:4][CH2:8][CH2:9][CH2:10][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 22477019Nickel monomethoxideHCID 705893803,4-Di-t-butyl-4-hydroxybenzyl alcohol

Product 2

HCID 356OctaneHCID 22477019Nickel monomethoxide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

[2,2'-thiobis-(4-t-octylphenolato)]-2-propanol nickel II (83.9 g) prepared as described in Example 4 was dissolved in benzene (250 ml) and 3,4-di-t-butyl-4-hydroxybenzyl alcohol (35.5 g) was added. The temperature of the mixture was raised to reflux and the resulting solution was refluxed for 2.25 hr. Displaced 2-propanol and benzene (150 ml) were then distilled from the reaction mixture. Remaining solvent was removed by rotary evaporation. From the residue the complex [2,2'-thiobis-(4-t-octylphenolato)]-3,4-di-t-butyl-4-hydroxybenzyl alcohol nickel II was obtained by recrystallization from n-octane as a green solid m.p. 253°-255° C.

Workup

  1. temperatureThe temperature of the mixture was raised
  2. temperatureto reflux
  3. temperaturethe resulting solution was refluxed for 2.25 hr
  4. distillationwere then distilled from the reaction mixture
  5. customRemaining solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-e9ec0fe38c8b486fa01b6538020fda03
Source dataset
uspto-grants-1980_04
Patent number
US04198303

Reaction notes

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