Hydrochloric Acid → 5-Cyclohexyl-2,2-dimethyl-5-(1-hydroxyethyl)-1,3-dioxane

HRID 2372416Notes

Reaction equation

HRID 2372416 reaction equation
[CH3:1][Mg]I.[CH:4]1([C:10]2([CH:18]=[O:19])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl>CCOCC>[CH:4]1([C:10]2([CH:18]([OH:19])[CH3:1])[CH2:15][O:14][C:13]([CH3:16])([CH3:17])[O:12][CH2:11]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 199044255-Cyclohexyl-2,2-dimethyl-5-formyl-1,3-dioxaneHCID 178418373HCID 178418373, compound

Product 1

HCID 199043995-Cyclohexyl-2,2-dimethyl-5-(1-hydroxyethyl)-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl magnesium iodide (3.0 ml, 3M solution in ether) was added to a solution of 5-cyclohexyl-2,2-dimethyl-5- formyl-1,3-dioxane (1.8 g.) in dry ether (50 ml.) The mixture was refluxed, with stirring, for two hours, cooled and poured into a mixture of 2N hydrochloric acid solution in ice. The aqueous mixture was extracted with ether. The ether extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. 5-Cyclohexyl-2,2-dimethyl-5-(1-hydroxyethyl)-1,3-dioxane was obtained as a cream solid (1.5 g.)

Workup

  1. temperaturewas refluxed
  2. temperaturecooled
  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. customevaporated in vacuo

Sources & evidence

ORD record
ord-2a5118fbc91d4390ba2a035d49128c66
Source dataset
uspto-grants-1992_03
Patent number
US05098929

Reaction notes

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