Chloride → HCID 66769688, compound

HRID 2063192Notes

Reaction equation

HRID 2063192 reaction equation
[C:1]12([C:14]([OH:16])=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([C:11]([OH:13])=[O:12])([CH2:4]3)[CH2:2]1)[CH2:8]2.S(Cl)(Cl)=O.C(O)C[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].N1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-].[CH2:37](Cl)Cl>>[C:1]12([C:14]([O:16][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])=[O:15])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][C:3]([C:11]([O:13][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:37])=[O:12])([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

7

Reactant 6

HCID 312ChlorideHCID 9571-OctanolHCID 1049PyridineHCID 6344Dichloromethane2×HCID 24386Thionyl ChlorideHCID 643391,3-Adamantanedicarboxylic acid

Product 1

HCID 66769688HCID 66769688, compound

Procedure

Di-n-hexyl 1,3-adamantanedicarboxylate is prepared by way of the following procedure: (A) A 100 mL round bottom flask equipped with a magnetic stir bar is charged with 1,3-admantanedicarboxylic acid (10.0 g, 44.6 mmol) and thionyl chloride (14.5 mL, 0.20 mole). The mixture is refluxed under nitrogen for 4 hrs and cooled to room temperature. Excess thionyl chloride is removed under vacuum and the solid chloride is used for the next step without further purification. (B) A 50 mL round bottom flask equipped with magnetic stirrer is charge with 1-octanol (5.2 g, 40.0 mmol), pyridine (3.24 mL, 40.0 mmol) in 50 mL of methylene chloride. The flask is cooled to 0° C. in ice-water bath, and 1,3-admantanedicarboxyl chloride (5.22 g, 20.0 mmol) in 10 mL of methylene chloride is added dropwise. The reaction mixture is stirred overnight at room temperature. The solvent is removed under vacuum and the residue is dissolved in 60 ml of ether, and filtered to remove solid. The filtrate is concentrated and purified with flash column chromatography to give pure product.

Workup

  1. temperatureThe mixture is refluxed under nitrogen for 4 hrs
  2. customExcess thionyl chloride is removed under vacuum
  3. customthe solid chloride is used for the next step without further purification
  4. custom(B) A 50 mL round bottom flask equipped with magnetic stirrer
  5. customThe solvent is removed under vacuum
  6. dissolutionthe residue is dissolved in 60 ml of ether
  7. filtrationfiltered
  8. customto remove solid
  9. concentrationThe filtrate is concentrated
  10. custompurified with flash column chromatography
  11. customto give pure product

Sources & evidence

ORD record
ord-695960677ed9456582bcaaed0b5387d0
Source dataset
uspto-grants-2012_10
Patent number
US08288304B2

Reaction notes

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