Carbon Dioxide → HCID 86742886, compound

HRID 1194950Notes

Reaction equation

HRID 1194950 reaction equation
[C:1]12(O)[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[C:2]2O.C(=O)=O.[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([OH:16])(=[O:15])[CH3:14].[C:13]([OH:16])(=[O:15])[CH3:14].[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2

Participants

5

Reactant 3

HCID 280Carbon Dioxide2×HCID 7918Acetic AnhydrideHCID 22155632HCID 22155632, compound

Product 1

HCID 86742886HCID 86742886, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 11 grams of norbornene diol (prepared as above) in 100 ml pyridine was cooled by dry ice. 45 ml of acetic anhydride was added to the cooled solution. The solution was held in the dry ice bath for about 30 minutes then allowed to sit at room temperature for about 16 hours, poured into an ice water slurry, extracted with chloroform and washed sequentially with 10% HCl, a saturated sodium bicarbonate solution, a sodium chloride solution, twice with water, then dried over sodium sulfate, and crystallized from a mixture of toluene and hexane to produce about 10 grams of norbornene diacetate.

Workup

  1. extractionextracted with chloroform
  2. washwashed sequentially with 10% HCl
  3. dry with materiala saturated sodium bicarbonate solution, a sodium chloride solution, twice with water, then dried over sodium sulfate
  4. customcrystallized from a mixture of toluene and hexane

Sources & evidence

ORD record
ord-f5625544d6e548e0a4fb365fcefd63b6
Source dataset
uspto-grants-1989_03
Patent number
US04816521

Reaction notes

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