Halite (NaCl) → 1,4-Dioxaspiro[4.6]undecan-7-ol

HRID 904

反应方程式

HRID 904 反应方程式
[O:1]1CCCC1.[CH2:6]1[O:16][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]2)[O:8][CH2:7]1.[BH4-].[Na+].[Cl-].[Na+]>O.[OH-].[Na+].C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH2:7]1[O:8][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]([OH:1])[CH2:10]2)[O:16][CH2:6]1

参与物

8

反应物 4

HCID 5234Halite (NaCl)HCID 8028四氢呋喃HCID 2794811,4-Dioxaspiro(4.6)undec-6-eneHCID 4311764硼氢化钠

产物 1

HCID 132988111,4-Dioxaspiro[4.6]undecan-7-ol

试剂、催化剂与溶剂 3

HCID 15337乙酸汞催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 14798二甲基对苯二胺二盐酸溶剂2 次

实验过程

Mercury(II) acetate (80.7 g, 0.25 mol) was dissolved in water (150 mL), then tetrahydrofuran (150 mL) was added to give a suspension. To this stirring suspension was added 2-cycloheptenone ethylene ketal (39 g, 0.25 mol). After stirring at ambient temperature for 3 hours, the mixture was cooled in an ice water bath. A 10% aqueous sodium hydroxide solution (150 mL) was added, followed by a solution of sodium borohydride (4.8 g, 0.13 mol) in 10% aqueous sodium hydroxide (150 mL). The mixture was allowed to reach ambient temperature and stirred overnight. The mixture was saturated with sodium chloride, stirred for 30 minutes, then allowed to settle; the solution was decanted into brine and extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo to give 3-hydroxycycloheptanone ethylene ketal (36 g).

后处理

  1. customto give a suspension
  2. temperaturethe mixture was cooled in an ice water bath
  3. customto reach ambient temperature
  4. stirringstirred overnight
  5. stirringstirred for 30 minutes
  6. customthe solution was decanted into brine
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-02e021bf3546479584ca183e01838f59
来源数据集
uspto-grants-1998_03
专利号
US05723462

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