Sulfuric Acid → 3-(1-Adamantyl)-4-methoxybenzoic acid

HRID 2051082Notes

Reaction equation

HRID 2051082 reaction equation
C(O[C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)(=O)C.CCCCCCC.S(=O)(=O)(O)O.[CH3:27][O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=1>C(O)C>[C:5]12([C:30]3[CH:31]=[C:32]([CH:36]=[CH:37][C:29]=3[O:28][CH3:27])[C:33]([OH:35])=[O:34])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 74784-Methoxybenzoic AcidHCID 8900HeptaneHCID 5199731-Adamantyl acetate

Product 1

HCID 52965033-(1-Adamantyl)-4-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 ml three-necked flask, and under a nitrogen environment, are placed 1 g of 1-acetoxyadamantane and 50 ml of n-heptane. After dissolution, 0.25 g of concentrated sulfuric acid is added drop by drop at a temperature of approximately 22° C. and 0.783 g of 4-methoxybenzoic acid is poured in slowly. After leaving the mixture well agitated for 48 hours, 50 ml of denatured ethanol are added and the insoluble material is filtered Concentration of the filtrate volume to three quarters yields a solid white precipitate which is filtered with sintered glass. It is dried in a vacuum oven for 24 hours at 30° C. and 0.680 g of expected raw product was collected (Melting point: 245°-246° C.).

Workup

  1. customIn a 100 ml three-necked flask, and under a nitrogen environment, are placed
  2. additionis poured in slowly
  3. customAfter leaving the mixture
  4. filtrationthe insoluble material is filtered Concentration of the filtrate volume to three quarters
  5. customyields a solid white precipitate which
  6. filtrationis filtered with sintered glass
  7. customIt is dried in a vacuum oven for 24 hours at 30° C.
  8. custom0.680 g of expected raw product was collected (Melting point: 245°-246° C.)

Sources & evidence

ORD record
ord-b57f06557a5d4955b526d18a5473bbc9
Source dataset
uspto-grants-1991_05
Patent number
US05015758

Reaction notes

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