Water → HCID 15068769, compound

HRID 346106Notes

Reaction equation

HRID 346106 reaction equation
[CH2:1]([C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)([CH2:6]3)[CH2:4]1)[CH2:10]2)[CH3:2].[OH2:19]>C(O)(=O)C.C(OC(=O)C)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[CH2:1]([C:3]12[CH2:4][C:5]3([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:11][CH:9]([CH2:8][C:7]([OH:19])([CH2:6]3)[CH2:12]1)[CH2:10]2)[CH3:2]

Participants

6

Reactant 2

HCID 962WaterHCID 13452199HCID 13452199, compound

Product 1

HCID 15068769HCID 15068769, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 0.03 mol of chromiumtrioxide, in 20 ml glacial acetic acid and 20 ml acetic anhydride, add 0.0095 mol of 1-ethyl-3-phenyl adamantane (II) at 0° C. and stir for 24 hours at 4° C. Pour the reaction mixture into water and extract with three portions of pentane. Wash the organic phase with saturated sodium chloride solution, dry over magnesium sulfate, filter and evaporate to dryness under vacuum. Hydrolize the residue with 20 ml of 2N NaOH and 50 ml of methanol. Remove the methanol under vacuum and dilute the residue with water. Then extract with three portions of ether. Dry the organic phase, filter and evaporate to dryness under vacuum. Recrystallize the residue from cyclohexane. (Yield: 50%).

Workup

  1. extractionextract with three portions of pentane
  2. washWash the organic phase with saturated sodium chloride solution
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter
  5. customevaporate to dryness under vacuum
  6. customRemove the methanol under vacuum
  7. additiondilute the residue with water
  8. extractionThen extract with three portions of ether
  9. customDry the organic phase
  10. filtrationfilter
  11. customevaporate to dryness under vacuum
  12. customRecrystallize the residue from cyclohexane

Sources & evidence

ORD record
ord-154dd8a710e840038b6e85dfd57fbd53
Source dataset
uspto-grants-1991_10
Patent number
US05061703

Reaction notes

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