Acetic Acid → 1,3-Di(4-carboxyphenyl)-5,7-dimethyl adamantane

HRID 1391357Notes

Reaction equation

HRID 1391357 reaction equation
CC1[CH:7]=[CH:6][C:5]([C:8]23[CH2:18][C:12]4([CH3:19])[CH2:13][C:14]([CH3:17])([CH2:16][C:10]([C:20]5[CH:25]=[CH:24]C(C)=[CH:22][CH:21]=5)([CH2:11]4)[CH2:9]2)[CH2:15]3)=[CH:4][CH:3]=1.[C:27]([OH:30])(=[O:29])[CH3:28].Cl.[C:32]([O:35]CC)(=[O:34])[CH3:33]>O.O.O.O.O.O.[Co](Br)Br>[C:27]([C:28]1[CH:3]=[CH:4][C:5]([C:8]23[CH2:18][C:12]4([CH3:19])[CH2:13][C:14]([CH3:17])([CH2:16][C:10]([C:20]5[CH:25]=[CH:24][C:33]([C:32]([OH:35])=[O:34])=[CH:22][CH:21]=5)([CH2:11]4)[CH2:9]2)[CH2:15]3)=[CH:6][CH:7]=1)([OH:30])=[O:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 213309991,3-Di(4-methylphenyl)-5,7-dimethyl adamantane

Product 1

HCID 213310071,3-Di(4-carboxyphenyl)-5,7-dimethyl adamantaneYield 82%

Reagents, catalysts & solvents 1

HCID 86641719Cobalt bromide, hexahydrateCatalyst

Procedure

In the method of Example III, 2.0 grams of 1,3-di(4-methylphenyl)-5,7-dimethyl adamantane were allowed to reflux with 300 ml of acetic acid containing 5.26 grams (0.022 moles) cobalt acetate tetrahydrate and, 2.39 grams cobalt bromide hexahydrate. An oxygen gas flow of 1 cubic foot per hour was bubbled through the refluxing mixture. Over a period of 6 hours, 5.39 grams of 1,3-di(4-methylphenyl)-5,7-dimethyl adamantane were added for a total of 7.39 grams. The reaction mixture was allowed to reflux an additional 28 hours. The reaction mixture was then mixed with water and the mixture was filtered. The resulting filter cake was dissolved in dilute sodium hydroxide. The filtrate was extracted with ether. The ether extracts was evaporated, but gave no residue. The basic solution was acidified with hydrochloric acid followed by an ethyl acetate extraction. Drying and concentration of the ethyl acetate gave 7.12 grams of 1,3-di(4-carboxyphenyl)-5,7-dimethyl adamantane (82% yield), M.P. 252°-255° C.

Workup

  1. customAn oxygen gas flow of 1 cubic foot per hour was bubbled through the refluxing mixture
  2. addition5.39 grams of 1,3-di(4-methylphenyl)-5,7-dimethyl adamantane were added for a total of 7.39 grams
  3. temperatureto reflux an additional 28 hours
  4. additionThe reaction mixture was then mixed with water
  5. filtrationthe mixture was filtered
  6. filtrationThe resulting filter cake
  7. dissolutionwas dissolved in dilute sodium hydroxide
  8. extractionThe filtrate was extracted with ether
  9. customThe ether extracts was evaporated
  10. customgave no residue
  11. extractionfollowed by an ethyl acetate extraction
  12. customDrying

Sources & evidence

ORD record
ord-a809731e40a64372b1ac3642a1fb8ea9
Source dataset
uspto-grants-1979_02
Patent number
US04142036

Reaction notes

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