Acetyl chloride → 1,3,5-Tris(acetyloxy)adamantane

HRID 1937258Notes

Reaction equation

HRID 1937258 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]12([OH:17])[CH2:14][C:9]3([OH:15])[CH2:10][CH:11]([CH2:13][C:7]([OH:16])([CH2:8]3)[CH2:6]1)[CH2:12]2>CN(C=O)C>[C:1]([O:17][C:5]12[CH2:14][C:9]3([O:15][C:9](=[O:15])[CH3:8])[CH2:10][CH:11]([CH2:13][C:7]([O:16][C:7](=[O:16])[CH3:6])([CH2:8]3)[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 98990221,3,5-Adamantanetriol

Product 1

HCID 147898361,3,5-Tris(acetyloxy)adamantaneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

In an atmosphere of nitrogen, 10 mmole of 1,3,5-adamantanetriol obtained by the method of Example 32 and 36 mmole of triethylamine were dissolved in 10 mL of DMF. To the mixture, 33 mmole of acetyl chloride was added dropwise over 30 minutes at 40° C. The mixture was stirred for another 3 hours at 40° C. As a result, the conversion of 1,3,5-adamantanetriol was 99%, and 1,3,5-tris(acetyloxy)adamantane (yield 95%) was formed.

Sources & evidence

ORD record
ord-0ca015df175f460bada8ce35b48d1d63
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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