Methanol → Heptanoic Acid

HRID 258390Notes

Reaction equation

HRID 258390 reaction equation
[CH2:1]([O:8]C(N1CCC2C(CO)(C2)C1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:22].OS(O)(=O)=O.O=[Cr](=O)=O.CO>CC(C)=O.O>[CH2:2]([C:1]([OH:8])=[O:22])[CH2:7][CH2:6][CH2:5][CH2:4][CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 20090024HCID 20090024, compoundHCID 131709961Jones' reagent

Product 1

HCID 8094Heptanoic AcidYield 93%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of the compound of Step 3 (580 mg, 2.22 mmol) in acetone (10 ml) was added Jones reagent (2.8 ml) at 0° C. The mixture was stirred at this temperature for 1 hour. After addition of methanol (5 ml), the reaction mixture was warmed to room temperature and diluted with water. The product was extracted into methylene chloride, and the combined organic layers were washed with brine and dried over magnesium sulfate. Removal of solvent in vacuo provided the title compound as a white solid, (570 mg, 2.1 mmol, 93% yield).

Workup

  1. extractionThe product was extracted into methylene chloride
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-8e9e598a6445407686ad13d005688582
Source dataset
uspto-grants-1993_11
Patent number
US05266569

Reaction notes

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