Sulfuric Acid → 2-(1-Adamantyl)-5-bromophenol

HRID 2294548Notes

Reaction equation

HRID 2294548 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]12(O)[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O.ClCCl>[C:9]12([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[OH:8])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 115633-BromophenolHCID 641521-AdamantanolHCID 516892Sodium Bicarbonate

Product 1

HCID 223478532-(1-Adamantyl)-5-bromophenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

17 g (0.1 mol) of 3-bromophenol, 15.22 g (0.1 mol) of 1-adamantanol and 50 ml of dichloromethane are introduced into a round-bottomed flask. 5 ml of concentrated sulphuric acid are added dropwise and the mixture is stirred at room temperature for 24 hours. The reaction medium is poured into water, the mixture is neutralized with sodium bicarbonate and extracted with ethyl ether and the organic phase is separated after settling has taken place, then dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of dichloromethane and hexane (50:50). After evaporation of the solvents, 15.2 g (50%) of the expected phenol, melting point 112°-114° C., are collected.

Workup

  1. extractionextracted with ethyl ether
  2. customthe organic phase is separated after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a silica column
  7. washeluted with a mixture of dichloromethane and hexane (50:50)
  8. customAfter evaporation of the solvents, 15.2 g (50%) of the expected phenol, melting point 112°-114° C.
  9. customare collected

Sources & evidence

ORD record
ord-4177b78d70a54328b4869e9f292a4b68
Source dataset
uspto-grants-1997_11
Patent number
US05688817

Reaction notes

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