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

HRID 1779232
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HRID 1779232 반응식
[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
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참가 물질

6

반응물 3

HCID 174Ethylene GlycolHCID 53629101MethylorthoformateHCID 90060223HCID 90060223, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 1140
Toluene
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4654297c0fc54958933b967b67d52830
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266853B2

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