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

HRID 1296383Notes

Reaction equation

HRID 1296383 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-e8c7deb546cf482abfda920855c922de
Source dataset
uspto-grants-2007_07
Patent number
USRE039744E1

Reaction notes

Loading…