Phenol → 4,4'-(1,3-Adamantanediyl)diphenol

HRID 1925196Notes

Reaction equation

[OH-:1].[Na+].Br[C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][C:6](Br)([CH2:7]3)[CH2:5]1)[CH2:11]2.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br-].[Br-].[Br-].[Al+3]>O>[OH:21][C:15]1[CH:20]=[CH:19][C:18]([C:4]23[CH2:13][CH:8]4[CH2:9][CH:10]([CH2:12][C:6]([C:4]5[CH:13]=[CH:8][C:7]([OH:1])=[CH:6][CH:5]=5)([CH2:7]4)[CH2:5]2)[CH2:11]3)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 500 mL five-neck flask equipped with a thermometer, an agitator, a reflux tube, a nitrogen introduction tube and an exhaust tube to a trap containing 30% aqueous sodium hydroxide was cooled in an ice bath. 6.47 g (0.022 mol) of 1,3-dibromo-adamantane, 200 ml of phenol and 2.6 g (0.01 mol) of aluminum tribromide were added to the flask and agitated at 0° C. for 6 hours. The mixture was heated to react at 60° C. for 4 hours. A reactant was poured into a 2,000 L of acid iced water. After the ice was melted, an organic layer was filtered, washed by pure water and saturated sodium chloride aqueous solution, and added into methanol so as to separate a product. The obtained product was dried under reduced pressure, thus obtaining 3.5 g of the product.

Workup

customA 500 mL five-neck flask equipped with a thermometer
temperaturewas cooled in an ice bath
temperatureThe mixture was heated
customto react at 60° C. for 4 hours
filtrationan organic layer was filtered
washwashed by pure water and saturated sodium chloride aqueous solution
additionadded into methanol so as
customto separate a product
customThe obtained product was dried under reduced pressure

Sources & evidence

ORD record: ord-a5b4e9a0ab3a4148ad224611bed0f1af
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178631B2

Reaction notes

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