Aluminum(III) Chloride → HCID 54314245, compound
Reaction equation
[CH2:1]([CH:18]1[CH:24]2[O:25][CH:21]([CH2:22][O:23]2)[CH2:20][O:19]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-]>C(OCC)C>[CH2:1]([CH:18]1[CH2:24][O:25][CH:21]([CH2:22][OH:23])[CH2:20][O:19]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
For each diastereomer of (4-heptadecyl-3,6,8-trioxabicyclo[3.2.1]octane, 260 mg of the diastereomer (0.73 mmol) was mixed with 48 mg of LiAlH4, in 5 mL of diethyl ether, and then refluxed gently. Dropwise, 15 mg (1.1 mmol) of AlCl3, in 5 mL of diethyl ether was added to the refluxing solution over a 5 minute period. The resulting reaction mixture was then refluxed vigorously over a period of about several hours. The reaction mixture was subsequently cooled to 0° C., quenched by the dropwise addition of ethylacetyl ether, and then mixed with 10 mL of water to form the associated diastereomers of 5-heptadecyl-2-hydroxy methyl-1,4-dioxane. This product was then extracted from the reaction mixture with diethyl ether and the product extract was subsequently dried and evaporated.
Workup
- temperaturerefluxed gently
- customThe resulting reaction mixture
- temperaturewas then refluxed vigorously over a period of about several hours
- customquenched by the dropwise addition of ethylacetyl ether
- additionmixed with 10 mL of water
Sources & evidence
- ORD record
- ord-0b94929fb19949eca2ad143cff5bd359
- Source dataset
- uspto-grants-1996_02
- Patent number
- US05489580
Reaction notes
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