Ethylene Glycol → Methyl 8-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-octanoate

HRID 1779232Notes

Reaction equation

HRID 1779232 reaction equation
[O:1]=[C:2]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH2:24](O)[CH2:25][OH:26].C([O-])([O-])OC>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:18]1([CH2:17][CH2:16][CH2:15][CH2:14][C:2]2([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[O:26][CH2:25][CH2:24][O:1]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 53629101MethylorthoformateHCID 90060223HCID 90060223, compound

Product 1

HCID 90060217Methyl 8-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-octanoateYield 92%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

Methyl 9-oxo-13-phenyl-tridecanoate (1.8 g, 5.65 mmol) was dissolved in toluene (5.0 mL), and ethylene glycol (0.935 mL, 16.8 mmol), methyl orthoformate (1.85 mL, 16.8 mmol), and p-toluenesulfonic acid monohydrate (53.0 mg, 0.279 mmol) were then added in order at room temperature. The mixture was stirred for 40 minutes, and then quenched with a saturated aqueous solution (30 mL) of sodium bicarbonate, and 10% methanol/ethyl acetate (100 mL) was then added. The mixture was separated. The organic layer was washed with a mixture of water (10 mL) and a saturated aqueous solution (30 mL) of sodium chloride, dried over anhydrous sodium sulfate, and filtered. The solvent was then distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 1.88 g (5.19 mmol, yield 92%) of methyl 8-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-octanoate.

Workup

  1. customquenched with a saturated aqueous solution (30 mL) of sodium bicarbonate, and 10% methanol/ethyl acetate (100 mL)
  2. additionwas then added
  3. customThe mixture was separated
  4. washThe organic layer was washed with a mixture of water (10 mL)
  5. dry with materiala saturated aqueous solution (30 mL) of sodium chloride, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customThe residue was purified on Biotage (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4654297c0fc54958933b967b67d52830
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

Loading…