Resorcinol → 4,6-Bis(adamantyl)resorcinol

HRID 1994653Notes

Reaction equation

HRID 1994653 reaction equation
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[OH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1>C1(C)C=CC=CC=1>[C:2]12([C:16]3[CH:17]=[C:18]([C:2]45[CH2:11][CH:6]6[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]6)[CH2:3]4)[CH2:9]5)[C:13]([OH:12])=[CH:14][C:15]=3[OH:19])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

4

Reactant 2

HCID 5054ResorcinolHCID 791061-Bromoadamantane

Product 1

HCID 235558344,6-Bis(adamantyl)resorcinolYield 69.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

75.0 g of 1-bromoadamantane (349 mmol), 9.58 g of 1,3-dihydroxybenzene (87.0 mmol), 25 mL of toluene and stirrer were charged in a 300 mL recovery flask and heated and agitated at 130° C. for 24 hours under nitrogen flow. A solvent was removed under reduced pressure to obtain a solid. The obtained solid was purified by column chromatography, thus obtaining 23.0 g of 4,6-di(1-adamantyl)-1,3-dihydroxybenzene (60.8 mmol; the yield was 69.9%).

Workup

  1. temperatureheated
  2. customA solvent was removed under reduced pressure
  3. customto obtain a solid
  4. customThe obtained solid was purified by column chromatography

Sources & evidence

ORD record
ord-f7f9acc8854c47f9b6335eb6e2319c28
Source dataset
uspto-grants-2010_01
Patent number
US07652125B2

Reaction notes

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