Sulfuric Acid → 3-(Adamantan-1-yl)-6-bromonaphthalen-2-ol

HRID 2051087Notes

Reaction equation

HRID 2051087 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.S(=O)(=O)(O)O.[OH:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([Br:31])[CH:25]=[CH:24]2>CCCCCCC>[C:5]12([C:30]3[CH:29]=[C:28]4[C:23]([CH:24]=[CH:25][C:26]([Br:31])=[CH:27]4)=[CH:22][C:21]=3[OH:20])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 271446-Bromo-2-naphthalenolHCID 5199731-Adamantyl acetate

Product 1

HCID 145490723-(Adamantan-1-yl)-6-bromonaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

In a 100 ml flask, under a nitrogen atmosphere, are placed 2 g of 1-acetoxyadamantane and 20 ml of n-heptane, and 0.5 g of concentrated sulfuric acid is introduced drop by drop. At a temperature of about 22.C, 2.3 of 6-hydroxy-2-bromonaphthalene are added slowly and the mixture is left in vigorous agitation. The solvent is eliminated by filtration and the solid residue in suspension in the water is collected. The residue is filtered and then washed until neutrality is obtained. The resulting reddish solid is washed again with hexane until a colorless filtrate is obtained. After drying in a vacuum oven for 24 hours at 30 C one obtains a raw product which is chromatographed with a silica column using an ethyl acetate and hexane mixture of 1:9 as the eluent. After evaporation of the solvents, 1.3 g of desired raw product were obtained (Melting point: 218°-224° C.).

Workup

  1. customIn a 100 ml flask, under a nitrogen atmosphere, are placed
  2. waitthe mixture is left in vigorous agitation
  3. filtrationThe solvent is eliminated by filtration
  4. customthe solid residue in suspension in the water is collected
  5. filtrationThe residue is filtered
  6. washwashed until neutrality
  7. customis obtained
  8. washThe resulting reddish solid is washed again with hexane until a colorless filtrate
  9. customis obtained
  10. customAfter drying in a vacuum oven for 24 hours at 30 C one
  11. customobtains a raw product which
  12. customis chromatographed with a silica column
  13. additionan ethyl acetate and hexane mixture of 1:9 as the eluent
  14. customAfter evaporation of the solvents

Sources & evidence

ORD record
ord-9825e678af9946ce8ecf05c101f5e088
Source dataset
uspto-grants-1991_05
Patent number
US05015758

Reaction notes

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