Acetic Acid → HCID 598893, compound

HRID 346098Notes

Reaction equation

HRID 346098 reaction equation
[C:1]1([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=[O:19])C>C(OC(=O)C)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[OH:19][C:11]12[CH2:12][CH:13]3[CH2:15][CH:9]([CH2:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([CH2:14]3)[CH2:16]1)[CH2:10]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 5226961-PHENYLADAMANTANE

Product 1

HCID 598893HCID 598893, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 0.03 mol chromiumtrioxide in 20 ml glacial acetic acid and 20 ml acetic anhydride, add 0.0095 mol of 1-phenyl adamantane at 0° C. and stir for 24 hours at 4° C. Pour the reaction mixture onto 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. Subsequently, 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. additionPour the reaction mixture onto water
  2. extractionextract with three portions of pentane
  3. washWash the organic phase with saturated sodium chloride solution
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. customevaporate to dryness under vacuum
  7. customSubsequently, remove the methanol under vacuum
  8. additiondilute the residue with water
  9. extractionThen extract with three portions of ether
  10. customDry the organic phase
  11. filtrationfilter
  12. customevaporate to dryness under vacuum
  13. customRecrystallize the residue from cyclohexane

Sources & evidence

ORD record
ord-aa18ca3d5d404683994a89d1cb7fe57f
Source dataset
uspto-grants-1991_10
Patent number
US05061703

Reaction notes

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