Ammonium Chloride → HCID 19904387, compound

HRID 2372410Notes

Reaction equation

HRID 2372410 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][C:6]1([CH3:16])[O:11][CH2:10][C:9]([CH2:14][CH3:15])([CH:12]=[O:13])[CH2:8][O:7]1.[Cl-].[NH4+]>O1CCCC1>[CH3:5][C:6]1([CH3:16])[O:7][CH2:8][C:9]([CH2:14][CH3:15])([CH:12]([OH:13])[CH2:1][CH3:2])[CH2:10][O:11]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 120128162,2-Dimethyl-5-ethyl-5-formyl-1,3-dioxaneHCID 178418443HCID 178418443, compound

Product 1

HCID 19904387HCID 19904387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl magnesium bromide (70 ml, 1.3M in tetrahydrofuran) was stirred at 0°, under nitrogen. 2,2-Dimethyl-5-ethyl-5-formyl-1,3-dioxane (10.3 g.) in dry tetrahydrofuran (20 ml.) was added and the mixture was stirred at room temperature for three hours. The mixture was then refluxed, with stirring, for one hour. Saturated aqueous ammonium chloride solution was added to the cooled reaction mixture. The aqueous mixture was extracted with ether. The ether extracts were washed with water, dried over anhydrous magnesium sulphate and the solvent was removed in vacuo. The residue was purified by chromatography on silica gel, eluting with 40% ether hexane. 2,2-Dimethyl-5-ethyl-5-(1-hydroxy propyl)-1,3-dioxane was obtained as a colourless oil (10.0 g.).

Workup

  1. temperatureThe mixture was then refluxed
  2. stirringwith stirring, for one hour
  3. extractionThe aqueous mixture was extracted with ether
  4. washThe ether extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with 40% ether hexane

Sources & evidence

ORD record
ord-46c030c3e804453dad481436c74f81e5
Source dataset
uspto-grants-1992_03
Patent number
US05098929

Reaction notes

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