Hydrochloric Acid → HCID 86675339, compound

HRID 1518891Notes

Reaction equation

HRID 1518891 reaction equation
[CH2:1]=[CH:2][CH:3]([OH:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].CC1(C)N([O])C(C)(C)CCC1.C([O-])(=[O:26])C.C([O-])(=O)C.C1([I+2])C=CC=CC=1.Cl>O1CCOCC1.O>[O:12]=[C:3]([CH:2]=[CH2:1])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:26])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2724126TempoHCID 10583334HCID 10583334, compoundHCID 178476573HCID 178476573, compound

Product 1

HCID 86675339HCID 86675339, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-decene-3,10-diol (920 mg, 5.34 mmol, 1.00 eq.) in 1,4-dioxane (15.0 mL) and H2O (10.0 mL), were added a catalytic amount of TEMPO and phenyliodine diacetate (2.06 g, 6.41 mmol, 1.20 eq.) at room temperature. The mixture was allowed to react at the same temperature for 20 hours, and then the reaction solution was poured into 1 M aqueous hydrochloric acid solution and a saturated salt solution. The organic phase was extracted with chloroform. Then, the resulting organic phase was dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=97:3) to obtain 8-oxo-9-decenoic acid as shown below (915 mg, 4.97 mmol, 93%).

Workup

  1. customto react at the same temperature for 20 hours
  2. extractionThe organic phase was extracted with chloroform
  3. dry with materialThen, the resulting organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=97:3)

Sources & evidence

ORD record
ord-88abcd971c524ab691e625c1acd8204f
Source dataset
uspto-grants-2015_07
Patent number
US09073802B2

Reaction notes

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