Phenol → 4,4'-(1,3-Adamantanediyl)diphenol
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]>>[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]=1Participants
Conditions
- Temperature
- 60 °C
Procedure
A 500 ml five-necked flask equipped with a thermometer, a stirrer, a reflux condenser, an inlet for nitrogen gas and a discharge pipe connected to a trap containing a 30% by weight aqueous solution of sodium hydroxide was cooled in an ice bath. Into the flask, 6.47 g (0.022 moles) of 1,3-dibromoadamantane, 200 ml of phenol and 2.6 g (0.01 mole) of aluminum tribromide were placed. The resultant mixture was stirred at 0° C. for 6 hours and, then, the reaction was allowed to proceed under heating at 60° C. for 4 hours. The reaction product was poured into 2,000 liters of acidic ice water. After the ice melted, an organic layer was taken out, washed with pure water and a saturated aqueous solution of sodium chloride and poured into methanol to separate the product. The obtained product was dried under a reduced pressure, and 3.5 g of a product was obtained.
Workup
- customA 500 ml five-necked flask equipped with a thermometer, a stirrer, a reflux condenser, an inlet for nitrogen gas
- customa discharge pipe connected to a trap
- temperaturewas cooled in an ice bath
- washwashed with pure water
- additiona saturated aqueous solution of sodium chloride and poured into methanol
- customto separate the product
- customThe obtained product was dried under a reduced pressure
Sources & evidence
- ORD record
- ord-e07396aaff6d440da73db7ae8df03a4e
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08337982B2
Reaction notes
Loading…