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

HRID 251714Notes

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

Conditions

Temperature: 155 °C

Procedure

In a 5 L recovery flask, 48.4 g of 3,3′-dibromo-5,5′,7,7′-tetramethyl-1,1′-biadamantane (100 mmol), 688 g of phenol (7.3 mol) and a stirrer were charged and agitated at 155° C. for 30 minutes under nitrogen flow. After cooling the mixture to room temperature, 4.3 L of ion-exchange water was added thereto and agitated at 80° C. for ten minutes. Solid precipitate was collected by filtration, then washed with 7 L of ion-exchange water and dried under reduced pressure, thus obtaining 50.6 g of 3,3′-bis(4-hydroxyphenyl)-5,5′,7,7′-tetramethyl-1,1′-biadamantane (99.0 mmol; yield: 99.0%).

Workup

temperatureAfter cooling the mixture to room temperature
stirringagitated at 80° C. for ten minutes
filtrationSolid precipitate was collected by filtration
washwashed with 7 L of ion-exchange water
customdried under reduced pressure

Sources & evidence

ORD record: ord-662ab2c2ce3042cdaf44c23f1b91f5dc
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863347B2

Reaction notes

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