Acetic Anhydride → HCID 14789836, compound

HRID 628554

Reaction equation

HRID 628554 reaction equation
[C:1]12([OH:13])[CH2:10][C:5]3([OH:11])[CH2:6][CH:7]([CH2:9][C:3]([OH:12])([CH2:4]3)[CH2:2]1)[CH2:8]2.C(O[C:18](=[O:20])[CH3:19])(=O)C>S(=O)(=O)(O)O>[C:5]([O:13][C:1]12[CH2:10][C:5]3([O:11][C:3](=[O:12])[CH3:2])[CH2:6][CH:7]([CH2:9][C:3]([O:12][C:18](=[O:20])[CH3:19])([CH2:4]3)[CH2:2]1)[CH2:8]2)(=[O:11])[CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 98990221,3,5-Adamantanetriol

Product 1

HCID 14789836HCID 14789836, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
100 °C

Procedure

92.12 g (0.5 mol) of 1,3,5-adamantanetriol are suspended in 153.14 g (1.5 mol) of acetic anhydride. Subsequently, 10 drops of concentrated sulfuric acid are added and the mixture is stirred on a rotary evaporator (without vacuum) until a homogeneous solution has formed. Subsequently, the mixture is heated to 100° C. under reflux for 2 h. After cooling, the reaction mixture is added to 300 ml of ice-water and extracted with dichloromethane. The combined organic phases are deacidified with sodium carbonate solution and washed with water. The mixture is dried over magnesium sulfate and filtered, and the solvent is removed under reduced pressure. 150.50 g (0.48 mol; 97.0%) of a colorless oil are obtained.

Workup

  1. customhas formed
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. extractionextracted with dichloromethane
  5. washwashed with water
  6. dry with materialThe mixture is dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed under reduced pressure
  9. custom150.50 g (0.48 mol; 97.0%) of a colorless oil are obtained

Sources & evidence

ORD record
ord-8407d9215afd483db461ba8f7c5e69fb
Source dataset
uspto-grants-2016_04
Patent number
US09314408B2

Linked notes

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