Acetic Anhydride → HCID 117774505, compound

HRID 921484Notes

Reaction equation

HRID 921484 reaction equation
[CH3:1][C:2]1[CH2:3][CH:4]2[CH:9]([CH2:10][CH:11]=1)[CH:8]1[CH2:12][CH:5]2[CH2:6][CH2:7]1.[NH4+].[OH-].C(O[C:19](=[O:21])[CH3:20])(=O)C>[Zn+2].[Br-].[Br-]>[CH3:1][C:2]1[CH:11]([C:19](=[O:21])[CH3:20])[CH2:10][CH:9]2[CH:4]([CH:3]=1)[CH:5]1[CH2:12][CH:8]2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 53632406HCID 53632406, compound

Product 1

HCID 117774505HCID 117774505, compound

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

ZnBr2 (3.0 g, 13.4 mmol) was added to a solution of acetic anhydride (30 mL) and 4-methyl-tricyclo[6.2.1.0(2,7)]undec-4-ene (10.0 g, 62 mmol) and then heated under reflux. After 2 hours at reflux the mixture was cooled then poured into dilute NH4OH (6%) and extracted with diethyl ether. The organic phase was washed with saturated NaHCO3, then brine, dried over Na2SO4, filtered and the solvents removed in vacuo. The crude ketone (9.3 g orange oil) was further purified by bulb to bulb distillation 0.1 mbar at 120° C. gave the desired ketone, 5.4 g as a mixture of isomers (7:6:16:21:16).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureAfter 2 hours at reflux the mixture
  4. temperaturewas cooled
  5. extractionextracted with diethyl ether
  6. washThe organic phase was washed with saturated NaHCO3
  7. dry with materialbrine, dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvents removed in vacuo
  10. distillationThe crude ketone (9.3 g orange oil) was further purified by bulb to bulb distillation 0.1 mbar at 120° C.

Sources & evidence

ORD record
ord-57e38804233741e298fa6fb7b9e71ecd
Source dataset
uspto-grants-2016_03
Patent number
US09273268B2

Reaction notes

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