Sodium Bicarbonate → HCID 90060287, compound

HRID 1779233Notes

Reaction equation

HRID 1779233 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[O:15][CH2:14][CH2:13][O:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].Cl[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])[O:15][CH2:14][CH2:13][O:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23665760Sodium HypochloriteHCID 90060222HCID 90060222, compound

Product 1

HCID 90060287HCID 90060287, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

8-[2-(4-Phenyl-butyl)-[1,3]dioxolan-2-yl]-octan-1-ol (830 mg, 2.48 mmol) was dissolved in toluene (4.2 mL), and 4-acetamide-2,2,6,6-tetramethylpiperidine 1-oxyl (2.6 mg, 0.0122 mmol) and an aqueous solution of 5% sodium bicarbonate (4.2 mL, 2.50 mmol) were then added. The mixture was then cooled to 0° C. An aqueous solution of 12% sodium hypochlorite (1.55 mL, 2.50 mmol) was added over 15 minutes. The mixture was then stirred at room temperature for 3 hours, and extracted twice with ethyl acetate (50 mL). The organic layer was then concentrated under reduced pressure. The residue was purified on Biotage (diol, n-hexane/ethyl acetate) to obtain 528 mg of the title compound (1.59 mmol, 64% yield).

Workup

  1. extractionextracted twice with ethyl acetate (50 mL)
  2. concentrationThe organic layer was then concentrated under reduced pressure
  3. customThe residue was purified on Biotage (diol, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-25fa63da575144809f396091fc4a55bf
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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