Phenol → 3,3'-Bis(4-hydroxyphenyl)(5,5',7,7'-tetramethyl)-1,1'-biadamantane

HRID 2195584Notes

Reaction equation

HRID 2195584 reaction equation
Br[C:2]12[CH2:12][C:6]3([CH3:13])[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([C:14]45[CH2:24][C:18]6([CH3:25])[CH2:19][C:20]([CH3:23])([CH2:22][C:16](Br)([CH2:17]6)[CH2:15]4)[CH2:21]5)([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:27]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O>[OH:33][C:27]1[CH:32]=[CH:31][C:30]([C:2]23[CH2:12][C:6]4([CH3:13])[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([C:14]56[CH2:24][C:18]7([CH3:25])[CH2:19][C:20]([CH3:23])([CH2:22][C:16]([C:30]8[CH:31]=[CH:32][C:27]([OH:33])=[CH:28][CH:29]=8)([CH2:17]7)[CH2:15]5)[CH2:21]6)([CH2:5]4)[CH2:3]2)[CH2:9]3)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 579347073,3'-Dibromo-5,5',7,7'-tetramethyl-1,1'-biadamantane

Product 1

HCID 688101083,3'-Bis(4-hydroxyphenyl)(5,5',7,7'-tetramethyl)-1,1'-biadamantaneYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Into a 5 liter four-necked separable flask equipped with a thermometer, a stirrer, an inlet for nitrogen gas and a reflux condenser, 48.4 g (0.1 mole) of 3,3′-dibromo-5,5′,7,7′-tetramethyl-1,1′-biadamantane and 688 g (7.3 moles) of phenol were placed, and the resultant mixture was heated under the refluxing condition at 155° C. for 30 minutes. After the mixture was cooled at the room temperature, 4.3 liters of pure water was added, and the obtained mixture was heated under the refluxing condition at 80° C. for 10 minutes. The formed precipitates were separated by filtration, and the solid substance was mixed with 7 liters of pure water and stirred for 10 minutes. The solid substance was separated by filtration and dried at 60° C. under a reduced pressure for 24 hours, and 50.6 g of 3,3′-bis(4-hydroxyphenyl)(5,5′,7,7′-tetramethyl)-1,1′-biadamantane was obtained (the yield: 99%).

Workup

  1. additionwas added
  2. customThe formed precipitates
  3. customwere separated by filtration
  4. additionthe solid substance was mixed with 7 liters of pure water
  5. customThe solid substance was separated by filtration
  6. customdried at 60° C. under a reduced pressure for 24 hours

Sources & evidence

ORD record
ord-cbe82a69c37d43e2a4018126d25bc9ef
Source dataset
uspto-grants-2012_12
Patent number
US08337982B2

Reaction notes

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