Glycerol → HCID 54090249, compound

HRID 483673Notes

Reaction equation

HRID 483673 reaction equation
C(Cl)Cl.[C:4]12([C:14](Cl)=[O:15])[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2.[OH:17][CH2:18][CH:19]([CH2:21][OH:22])[OH:20]>N1C=CC=CC=1>[C:4]12([C:14]([O:17][CH2:18][CH:19]([CH2:21][O:22][C:14]([C:4]34[CH2:13][CH:8]5[CH2:7][CH:6]([CH2:12][CH:10]([CH2:9]5)[CH2:11]3)[CH2:5]4)=[O:15])[OH:20])=[O:15])[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2

Participants

5

Reactant 3

HCID 753GlycerolHCID 6344DichloromethaneHCID 989151-Adamantanecarbonyl chloride

Product 1

HCID 54090249HCID 54090249, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a flask under nitrogen 1.053 gms of glycerol is dissolved in 4 ml of pyridine and 6 ml of methylene chloride and cooled to about -10° C. Then 5.00 gms of (1-adamantanoyl)-chloride (Aldrich Chemical Co.) is added in one portion and stirring is continued for about half an hour with cooling and then another two hours at ambient temperature. The resulting solid is filtered and washed with methylene chloride. The combined organic layers are washed twice with dilute aqueous HCl and then once with water and dried over magnesium sulfate. 1,3-di(1-adamantanoyl) glycerol is isolated as an oil.

Workup

  1. waitis continued for about half an hour
  2. temperaturewith cooling
  3. customanother two hours
  4. customat ambient temperature
  5. filtrationThe resulting solid is filtered
  6. washwashed with methylene chloride
  7. washThe combined organic layers are washed twice with dilute aqueous HCl
  8. dry with materialonce with water and dried over magnesium sulfate

Sources & evidence

ORD record
ord-e5974c32c5724e8abd0c161eb183d775
Source dataset
uspto-grants-1993_07
Patent number
US05225590

Reaction notes

Loading…