Ethyl Acetate → 5-Hexadecyloxymethyl-2-phenyl-1,3-dioxane

HRID 728494Notes

Reaction equation

HRID 728494 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1.[H-].[Na+].CS(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])(=O)=O.C(OCC)(=O)C>C1C=CC=CC=1>[CH2:37]([O:1][CH2:2][CH:3]1[CH2:4][O:5][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][CH2:8]1)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 519810Hexadecyl methanesulfonateHCID 10679342(2-Phenyl-1,3-dioxan-5-yl)methanol

Product 1

HCID 198842025-Hexadecyloxymethyl-2-phenyl-1,3-dioxaneYield 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 7.769 g (40 mM) of 5-hydroxymethyl-2-phenyl-1,3-dioxane n1 and 2.08 g (52 mM) of 60% sodium hydride in oil in 150 ml of anhydrous benzene is heated at 50° C. for 1 hour then a solution of 17.28 g (54 mM) of n-hexadecyl methanesulfonate in 50 ml of anhydrous benzene is added. The reaction mixture is heated under refluxing for 7 hours. The product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. Crystallization of the residue from n-pentane-methanol affords 16.203 g (97% yield) of the titled compound n2.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder refluxing for 7 hours
  3. washThe ethyl acetate layer is washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customCrystallization of the residue from n-pentane-methanol

Sources & evidence

ORD record
ord-77066b4b4e9243eaa30cff8652522946
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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