Sulfuric Acid → 2-(1-Adamantyl)-4-bromophenol

HRID 2051081Notes

Reaction equation

HRID 2051081 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:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1>C(O)C>[C:5]12([C:32]3[CH:33]=[C:28]([Br:27])[CH:29]=[CH:30][C:31]=3[OH:34])[CH2:12][CH:11]3[CH2:10][CH:9]([CH2:8][CH:7]([CH2:13]3)[CH2:6]1)[CH2:14]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 78084-BromophenolHCID 8900HeptaneHCID 5199731-Adamantyl acetate

Product 1

HCID 46704942-(1-Adamantyl)-4-bromophenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

In a 100 ml three-necked flask, and under a nitrogen environment, is placed 1 g of 1-acetoxyadamantane and 10 ml of n-heptane. After total dissolution, 0.25 g of concentrated sulfuric acid is added drop by drop while keeping the temperature at 20° C., then 0.886 g of 4bromophenol is poured in slowly. After leaving 24 hours in vigorous agitation, 20 ml of denatured ethanol are added while maintaining the temperature at 20° C. Next, the solvent is evaporated to dryness under reduced pressure and a whitish raw product is obtained. The product is redissolved in water at approximately 60° C., it is washed to pH 6 and dried in a vacuum oven for 24 hours at 25° C. One collected 1.24 g of expected raw product (Melting point: 140°-141° C.).

Workup

  1. customIn a 100 ml three-necked flask, and under a nitrogen environment, is placed
  2. additionis added drop by drop
  3. customat 20° C.
  4. additionare added
  5. customNext, the solvent is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8e8b0194384242f78c15282a4df3a6d0
Source dataset
uspto-grants-1991_05
Patent number
US05015758

Reaction notes

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