Sulfuric Acid → HCID 14549073, compound

HRID 2051088Notes

Reaction equation

HRID 2051088 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.[Br:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:38][CH3:39])[CH:34]=2)[CH:29]=1>C(O)C>[C:5]12([C:32]3[CH:31]=[C:30]4[C:35]([CH:36]=[CH:37][C:28]([Br:27])=[CH:29]4)=[CH:34][C:33]=3[O:38][CH3:39])[CH2:6][CH:7]3[CH2:13][CH:11]([CH2:10][CH:9]([CH2:8]3)[CH2:14]1)[CH2:12]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8900HeptaneHCID 787862-Bromo-6-methoxynaphthaleneHCID 5199731-Adamantyl acetate

Product 1

HCID 14549073HCID 14549073, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 ml flask, under a nitrogen atmosphere, are placed 1 g of 1-acetoxyadamantane and 30 ml of n-heptane, and 0.25 g of concentrated sulfuric acid is introduced. At a temperature of about 20° C., 1.22 g of 2-bromo-6-methoxynaphthalene are poured in slowly and the mixture is left in vigorous agitation for 48 hours. Next, 20 ml of denatured ethanol are introduced and the mixture is evaporated to dryness under reduced pressure. The product is taken up in denatured ethanol and the precipitate is filtered with sintered glass. After drying of the raw product in a vacuum oven for 24 hours at 30° C., one purifies using silica column chromatography. There were obtained 0.4 g of the desired raw product (Melting point: 164°-168° C.).

Workup

  1. customIn a 100 ml flask, under a nitrogen atmosphere, are placed
  2. customthe mixture is evaporated to dryness under reduced pressure
  3. filtrationthe precipitate is filtered with sintered glass
  4. dry with materialAfter drying of the raw product in a vacuum oven for 24 hours at 30° C.

Sources & evidence

ORD record
ord-c95db27efb8940b093a879dbaa879e0d
Source dataset
uspto-grants-1991_05
Patent number
US05015758

Reaction notes

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