Toluene → HCID 86623820, compound

HRID 1994658Notes

Reaction equation

Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([C:12]45[CH2:21][CH:16]6[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]6)[CH2:13]4)[CH2:19]5)([CH2:5]3)[CH2:3]1)[CH2:9]2.[OH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=1.[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:30]12([C:6]34[CH2:7][CH:8]5[CH2:9][CH:2]([CH2:3][C:4]([C:26]6[CH:27]=[C:28]([C:2]78[CH2:11][CH:6]9[CH2:7][CH:8]([CH2:10][C:4]([C:12]%10%11[CH2:21][CH:16]%12[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]%12)[CH2:13]%10)[CH2:19]%11)([CH2:5]9)[CH2:3]7)[CH2:9]8)[C:23]([OH:22])=[CH:24][C:25]=6[OH:29])([CH2:10]5)[CH2:5]3)[CH2:11]4)[CH2:36][CH:12]3[CH2:13][CH:34]([CH2:33][CH:32]([CH2:19]3)[CH2:31]1)[CH2:35]2

Participants

Reactant 3

HCID 1140Toluene

HCID 5054Resorcinol

HCID 15529893HCID 15529893, compound

Product 1

HCID 86623820HCID 86623820, compoundYield 66.4%

Conditions

Temperature: 130 °C

Procedure

121.9 g of 3-bromo-1,1′-biadamantane (349 mmol), 9.58 g of 1,3-dihydroxybenzene (87.0 mmol), 25 mL of toluene and a stirrer were charged in a 300 mL recovery flask. The mixture was heated and agitated at 130° C. for 24 hours under nitrogen flow. A solid was obtained by removing a solvent under reduced pressure. The obtained solid was purified by column chromatography, thus obtaining 37.4 g of 4,6-di[3-(1-adamantyl)-(1-adamantyl)]-1,3-dihydroxybenzene (57.8 mmol; the yield was 66.4%).

Workup

temperatureThe mixture was heated
customA solid was obtained
customby removing a solvent under reduced pressure
customThe obtained solid was purified by column chromatography

Sources & evidence

ORD record: ord-4d91b94eecdc453ca3f2bb418458aa9e
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652125B2

Reaction notes

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