Water → Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylate

HRID 546163노트

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HRID 546163 반응식
[CH2:1]([O:3][C:4]([C:6]1(C(OCC)=O)[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8][CH2:7]1)=[O:5])[CH3:2].[Cl-].[Na+].O>CS(C)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][O:10][C:9]([CH3:12])([CH3:13])[O:8][CH2:7]1)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 5234Sodium Chloride2회HCID 287722Diethyl 2,2-dimethyl-1,3-dioxane-5,5-dicarboxylate

생성물 1

HCID 11019611Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylate수율 53%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To the solution of 2,2-dimethyl-[1,3]dioxane-5,5-dicarboxylic acid diethyl ester (19.75 g, 75.96 mmol) in dimethyl sulfoxide (80 ml) was added sodium chloride (4.4 g, 75.76 mmol) and water (2 ml). The reaction was refluxed for 7 h. After such time, it was poured into saturated sodium chloride solution (500 ml) and extracted with ether (4×200 ml). The combined organics were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residual oil was distilled under reduced pressure. Three fractions collected between 100° C. and 120° C. were combined to afford 2,2-dimethyl-[1,3]dioxane-5-carboxylic acid ethyl ester (7.58 g, 53%) as a clear oil (J. Org. Chem. 1986, 51, 2637) 1H NMR (300 MHz, CDCl3) δ ppm 1.26 (t, J=7.1 Hz, 3H, CH3), 1.41 (s, 3H, CH3), 1.44 (s, 3H, CH3), 2.74-2.85 (m, 1H, CH), 3.96-4.30 (m, 6H, 3×OCH2).

후처리

  1. temperatureThe reaction was refluxed for 7 h
  2. extractionextracted with ether (4×200 ml)
  3. washThe combined organics were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. distillationThe residual oil was distilled under reduced pressure
  8. customThree fractions collected between 100° C. and 120° C.

출처 및 근거

ORD 기록
ord-8fec9f8ccf214b41a59022ade651467b
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935699B2

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